AU2017379281A1 - Substituted heteroaryl pyrrolones and salts thereof and use thereof as herbicidal active substances - Google Patents

Substituted heteroaryl pyrrolones and salts thereof and use thereof as herbicidal active substances Download PDF

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AU2017379281A1
AU2017379281A1 AU2017379281A AU2017379281A AU2017379281A1 AU 2017379281 A1 AU2017379281 A1 AU 2017379281A1 AU 2017379281 A AU2017379281 A AU 2017379281A AU 2017379281 A AU2017379281 A AU 2017379281A AU 2017379281 A1 AU2017379281 A1 AU 2017379281A1
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alkyl
methyl
cio
aryl
butenyl
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AU2017379281A
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Hansjörg Dietrich
Jens Frackenpohl
Jana FRANKE
Elmar Gatzweiler
Hendrik Helmke
Peter Lümmen
Anu Bheemaiah MACHETTIRA
Anna Maria REINGRUBER
Christopher Hugh Rosinger
Dirk Schmutzler
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Bayer AG
Bayer CropScience AG
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Bayer AG
Bayer CropScience AG
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    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/48—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with two nitrogen atoms as the only ring hetero atoms
    • A01N43/50—1,3-Diazoles; Hydrogenated 1,3-diazoles
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    • C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
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    • C07D417/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings directly linked by a ring-member-to-ring-member bond
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    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
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    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/48—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with two nitrogen atoms as the only ring hetero atoms
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    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/64—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with three nitrogen atoms as the only ring hetero atoms
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    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/64—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with three nitrogen atoms as the only ring hetero atoms
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    • A01N43/653—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles
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    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/713—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with four or more nitrogen atoms as the only ring hetero atoms
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    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/72—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms
    • A01N43/74—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms five-membered rings with one nitrogen atom and either one oxygen atom or one sulfur atom in positions 1,3
    • A01N43/76—1,3-Oxazoles; Hydrogenated 1,3-oxazoles
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    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/72—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms
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    • A01N43/78—1,3-Thiazoles; Hydrogenated 1,3-thiazoles
    • A—HUMAN NECESSITIES
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    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/72—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms
    • A01N43/80—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms five-membered rings with one nitrogen atom and either one oxygen atom or one sulfur atom in positions 1,2
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
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    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
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    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/72—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms
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    • C07D513/04—Ortho-condensed systems

Abstract

The invention relates to substituted heteroaryl pyrrolones of general formula (I) and salts thereof, wherein the groups of general formula (I) are defined as cited in the description, and to the use thereof as herbicides, in particular for controlling weeds and/or weed grasses in crops of useful plants and/or as plant growth regulators for influencing the growth of crops of useful plants.

Description

WO 2018/114596
PCT/EP2017/082832
Substituted heteroaryl pyrrolones and salts thereof and use thereof as herbicidal active substances
Description
The invention relates to the technical field of crop protection agents, in particular that of herbicides for the selective control of broad-leaved weeds and weed grasses in crops of useful plants.
Specifically, the present invention relates to substituted heteroarylpyrrolones and salts thereof, to processes for their preparation and to their use as herbicides.
In their application, crop protection agents known to date for the selective control of harmful plants in crops of useful plants or active compounds for controlling unwanted vegetation sometimes have disadvantages, be it (a) that they have no or else insufficient herbicidal activity against particular harmful plants, (b) that the spectrum of harmful plants which can be controlled with an active compound is not wide enough, (c) that their selectivity in crops of useful plants is too low and/or (d) that they have a toxicologically unfavourable profile. Furthermore, some active compounds which can be used as plant growth regulators for a number of useful plants cause unwanted reduced harvest yields in other useful plants or are not compatible with the crop plant, or only within a narrow application rate range. Some of the known active compounds cannot be produced economically on an industrial scale owing to precursors and reagents which are difficult to obtain, or they have only insufficient chemical stabilities. In the case of other active compounds, the activity is too highly dependent on environmental conditions, such as weather and soil conditions.
The herbicidal activity of these known compounds, in particular at low application rates, and/or their compatibility with crop plants remain deserving of improvement.
Various documents describe substituted pyrrolones and hydantoins having herbicidal properties. WO2016/071359 and W02016/071360 disclose pyrrolones carrying heterocyclic substituents at the nitrogen including, for example, isoxazolines which are optionally substituted further. Furthermore, substituted pyrrolones and their herbicidal or pesticidal properties are described in CH633678, DE 2735841, DE, EP0297378, EP0334133, EP0339390 and EP0286816. Additionally, WO2016/071361, WO2016/071362, WO2016/071363 and WO2016/071364 describe substituted hydantoins which also carry heterocyclic substituents at the nitrogen, for example isoxazolines which are optionally substituted further. Selected specifically substituted 1,3,4-thiadiazolyl- and l,2,4-thiadiazolyl-2,5-dioxoimidazolines and their herbicidal action are described in DE2247266. Substituted pyrazolylpyrrolones and their use as herbicidally active compounds are described, for example, in WO2015/018434.
WO 2018/114596
PCT/EP2017/082832
Furthermore, it is known that certain substituted carbamoyloxypyrrolones and phenyloxypyrrolones can be employed as growth regulators or germination stimulators (cf. W02014/131843 and WO2015/128321). The structural motive of the hydroxypyrrolones is also found in substances isolated from Lilium candidum, for example l,5-dihydro-5-hydroxy-3,4 ‘-dimethyl-[ 1,2‘-bi-2H-pyrrolo]5 2,5‘(l'H)-dione (cf. Ceska a Slovenska Farmacie, 2007, 56, 27; Neoplasma, 2000, 47, 313).
However, the use of heteroarylpyrrolones monosubstituted at the C-C double bond or of salts thereof as herbicidally active compounds has hitherto not been described. Surprisingly, it has now been found that heteroarylpyrrolones monosubstituted at the C-C double bond or salts thereof are particularly suitable as 10 herbicides.
Accordingly, the present invention provides substituted heteroarylpyrrolones of the general formula (I) or salts thereof
W.
Figure AU2017379281A1_D0001
Figure AU2017379281A1_D0002
(I) in which
Q represents the moieties Q-1 to Q-29
WO 2018/114596
PCT/EP2017/082832
4)=N 4/ X 7 4/ X 7 p4
R4 R R R R R R7
Q-1 Q-2 Q-3 Q-4 Q-5
:£r A- ,)=N n 4/ X 7 ύγ
R4 R R R r4/ R7
Q-6 Q-7 Q-8 Q-9 Q-10
,/- n iF 4/ X 7 4/ \ 7 p7 Y-X 4/ '5 p4 ΥΓ 5/ X 7
R R R R R R R R R
Q-11 Q-12 Q-13 Q-14 „4 Q-15
A'A4 'AfeN 4 D4 O R R7-yyN—N 'r5 N Ox '-C
Q-16 Q-17 Q-18 Q-19 Q-20
Figure AU2017379281A1_D0003
Q-21 Q-22
R4' N'R 5 _N N—N 'r5
Q-26 Q-27
Figure AU2017379281A1_D0004
A1, A2, A3, A4 are identical or different and independently of one another represent N (nitrogen) or the moiety C-R8, but there are never more than two adjacent nitrogen atoms, and where R8 in the 5 moiety C-R8 in each case has identical or different meanings according to the definition below,
X and Y independently of one another represent C-H or the moiety C-R1, where
X represents C-H if Y represents the moiety C-R1 and
X represents the moiety C-R1 if Y represents C-H,
R1 represents halogen, (Ci-Cs)-alkyl, (Ci-Cs)-haloalkyl, (Ci-Cs)-hydroxyalkyl, (Ci-Cs)-alkoxyalkyl, (Ci-Cs)-alkoxy, (Ci-Cs)-haloalkoxy, (Ci-Cs)-alkylthio, (Ci-Cs)-haloalkylthio, aryl, heteroaryl,
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R3 represents hydroxy, hydrothio, halogen, NR10Rn, (Ci-Cs)-alkoxy, (C3-Cio)-cycloalkyl-(Ci-Cs)alkoxy, aryl-(Ci-Cs)-alkoxy, (Ci-Cs)-alkoxy-(Ci-Cs)-alkoxy, arylcarbonyloxy, (Ci-Cs)alkylcarbonyloxy, aryl-(Ci-Cs)-alkylcarbonyloxy, heteroarylcarbonyloxy, (C3-C10)cycloalkylcarbonyloxy, heterocyclylcarbonyloxy, (Ci-Cs)-haloalkylcarbonyloxy, (C2-Cs)alkenylcarbonyloxy, OC(O)OR12, OC(O)SR12, OC(S)OR12, OC(S)SR12, OSO2R13, OSO2OR12, OCHO,
R4 and R7 independently of one another represent hydrogen, hydrothio, hydroxy, halogen, (Ci-Cs)-alkyl, (Ci-Cs)-haloalkyl, (C3-Cio)-cycloalkyl, (C3-Cio)-cycloalkyl-(Ci-Cs)-alkyl, aryl, heteroaryl, heterocyclyl, aryl-(Ci-Cs)-alkyl, heteroaryl-(Ci-Cs)-alkyl, heterocyclyl-(Ci-Cs)-alkyl, (C2-Cs)alkenyl, (C2-Cs)-alkynyl, (C2-Cs)-haloalkenyl, (C2-Cs)-haloalkynyl, (C3-Cio)-halocycloalkyl, (C4-Cio)-cycloalkenyl, (C4-Cio)-halocycloalkenyl, aryl-(C2-Cs)-alkenyl, heteroaryl-(C2-Cs)alkenyl, heterocyclyl-(C2-Cs)-alkenyl, aryl-(C2-Cs)-alkynyl, heteroaryl-(C2-Cs)-alkynyl, heterocyclyl-(C2-Cs)-alkynyl, (C3-Cio)-cycloalkyl-(C2-Cs)-alkynyl, arylcarbonyl-(Ci-Cs)-alkyl, (Ci-Cs)-alkylcarbonyl-(Ci-Cs)-alkyl, heteroarylcarbonyl-(Ci-Cs)-alkyl, (C3-C10)cycloalkylcarbonyl-(Ci-Cs)-alkyl, aryl-(Ci-Cs)-alkoxycarbonyl-(Ci-Cs)-alkyl, (Ci-Cs)alkoxycarbonyl-(Ci-Cs)-alkyl, (Ci-Cs)-alkoxy-(Ci-Cs)-alkyl, arylcarbonyloxy-(Ci-Cs)-alkyl, heteroarylcarbonyloxy-(Ci-Cs)-alkyl, heterocyclylcarbonyloxy-(Ci-Cs)-alkyl, (Ci-Cs)alkylcarbonyloxy-(Ci-Cs)-alkyl, (C3-Cs)-cycloalkylcarbonyloxy-(Ci-Cs)-alkyl, (Ci-Cs)haloalkoxy-(Ci-Cs)-alkyl, aryl-(Ci-Cs)-alkoxy-(Ci-Cs)-alkyl, heteroaryl-(Ci-Cs)-alkoxy-(Ci-Cs)alkyl, CHO, C(O)R12, C(O)OR12, C(O)NR10Rn, OR12, SR13, SOR13, SO2R13, NR10Rn, R10RnN(Ci-Cs)-alkyl, cyano-(Ci-Cs)-alkyl, hydroxycarbonyl-(Ci-Cs)-alkyl, hydroxycarbonyl, (Ci-Cs)haloalkoxy-(Ci-Cs)-alkylthio, (Ci-Cs)-alkylthio-(Ci-Cs)-alkylene, (Ci-Cs)-haloalkylthio-(Ci-Cs)alkylthio, (Ci-Cs)-alkylthio-(Ci-Cs)-alkylthio, aminocarbonyl, aminocarbonyl-(Ci-Cs)-alkyl, (Ci-Cs)-alkylaminocarbonyl-(Ci-Cs)-alkyl, (C3-C8)-cycloalkylaminocarbonyl-(Ci-Cs)-alkyl, (C2C8)-alkenyloxycarbonyl-(Ci-C8)-alkyl, (C3-C8)-cycloalkyl- (Ci-C8)-alkoxycarbonyl-(Ci-C8)alkyl, cyano, hydroxy-(Ci-C8)-alkyl, (C2-C8)-alkenyloxy-(Ci-C8)-alkyl, or where R4 and R7 together with the carbon atom to which they are respectively attached form a partially saturated ring having a total of 3 to 7 members which is optionally interrupted by one to three heteroatoms from the group consisting of N, O and S and optionally substituted further, if Q represents Q-3, Q-4, Q-8, Q-9, Q-12 or Q-19,
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R5 represents hydrogen, formyl, (Ci-Cs)-alkyl, (Ci-Cs)-haloalkyl, hydroxy-(Ci-C8)-alkyl, hydroxycarbonyl-(Ci-Cs)-alkyl, (Ci-C8)-alkoxy-(Ci-C8)-alkyl, (C3-Cio)-cycloalkyl, (C3-C10)halocycloalkyl, aryl, heteroaryl, (C3-Cio)-cycloalkyl-(Ci-C8)-alkyl, heterocyclyl, (C2-Q)alkenyl, (C2-C8)-alkynyl, NR10Rn, aryl-(Ci-C8)-alkyl, heteroaryl-(Ci-C8)-alkyl, heterocyclyl(Ci-Cs)-alkyl, (Ci-Cs)-cyanoalkyl, C(O)R12, C(O)OR12, C(O)NR10R11, SO2R13, (Ci-C8)alkoxycarbonyl-(Ci-Cs)-alkyl, (C2-C8)-alkenyloxycarbonyl-(Ci-C8)-alkyl, aryl-(Ci-Cs)alkoxycarbonyl-(Ci-Cs)-alkyl, heteroaryl-(Ci-C8)-alkoxycarbonyl-(Ci-C8)-alkyl, aryloxycarbonyl-(Ci-Cs)-alkyl, arylcarbonyl-(Ci-C8)-alkyl, (Ci-C8)-alkylcarbonyl-(Ci-C8)-alkyl, heteroarylcarbonyl-(Ci-C8)-alkyl, heterocyclylcarbonyl-(Ci-C8)-alkyl, or where R4 and R5 together with the nitrogen atom or carbon atom to which they are respectively attached form a partially saturated ring having a total of 3 to 7 members which is optionally interrupted by one to three heteroatoms from the group consisting of N, O and S and optionally substituted further, if Q represents Q-13, Q-14 or Q-15,
R6 represents hydrogen or (Ci-Cs)-alkyl,
R8 represents hydrogen, halogen, cyano, nitro, hydrothio, hydroxy, NR10RH, OR12, SR13, SOR13, SO2R13, thiocyanate, isothiocyanate, formyl, (Ci-Cs)-alkyl, (C2-C8)-alkenyl, (C2-C8)-alkynyl, (Ci-Cio)-haloalkyl, (C2-C8)-haloalkenyl, (C2-C8)-haloalkynyl, (C3-Cio)-cycloalkyl, (C3-C10)halocycloalkyl, (C4-Cio)-cycloalkenyl, (C4-Cio)-halocycloalkenyl, pentafluorothio, (Ci-C8)alkoxy-(Ci-Cs)-haloalkyl, (Ci-C8)-haloalkoxy-(Ci-C8)-haloalkyl, (Ci-C8)-haloalkoxy-(Ci-C8)alkyl, aryl, aryl-(Ci-C8)-alkyl, heteroaryl, heteroaryl-(Ci-C8)-alkyl, (C3-C8)-cycloalkyl-(Ci-C8)alkyl, (C4-Cio)-cycloalkenyl-(Ci-C8)-alkyl, heterocyclyl, heterocyclyl-(Ci-C8)-alkyl, (Ci-C8)alkoxy-(Ci-Cs)-alkyl, (Ci-C8)-alkyltitio-(Ci-C8)-alkyl, (Ci-C8)-hatealkylthio-(Ci-C8)-alkyl, (CiC8)-alkylcarbonyl-(Ci-C8)-alkyl, C(O)OR12, C(O)NR10R11, C(O)R12, -C=NOR12, -C=NOH, R10RnN-(Ci-C8)-alkyl, R12O(O)C-(Ci-C8)-alkyl, hydroxycarbonyl, hydroxycarbonyl(Ci-C8)-alkyl, aryl-(Ci-C8)-alkynyl, heteroaryl-(Ci-C8)-alkynyl, heterocyclyl-(Ci-C8)-alkynyl, tris-[(Ci-C8)-alkyl]silyl-(C2-C8)-alkynyl, bis-[(Ci-C8)-alkyl](aryl)silyl-(C2-C8)-alkynyl, bisaryl[(Ci-C8)-alkyl]silyl-(C2-C8)-alkynyl, (C3-C8)-cycloalkyl-(C2-C8)-alkynyl, aryl-(C2-C8)alkenyl, heteroaryl-(C2-C8)-alkenyl, heterocyclyl-(C2-C8)-alkenyl, (C3-C8)-cycloalkyl-(C2-C8)alkenyl, (Ci-C8)-alkoxy-(Ci-C8)-alkoxy-(Ci-C8)-alkyl, (Ci-C8)-alkylaminosulfonylamino, (C3C8)-cycloalkylaminosulfonylamino, diazo, aryldiazo, tris-[(Ci-C8)-alkyl]silyl, bis-[(Ci-C8)alkyl](aryl)silyl, bis-aryl[(Ci-C8)-alkyl]silyl, or where A1 and A2, when each is a group C-R8, together with the atoms to which they are attached form a partially saturated or fully unsaturated 5- to 7-membered ring which is
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R10 and R11 are identical or different and independently of one another represent hydrogen, (Ci-Cs)alkyl, (C2-Cs)-alkenyl, (C2-Cs)-alkynyl, (Ci-Cs)-cyanoalkyl, (Ci-Cio)-haloalkyl, (C2-Cs)haloalkenyl, (C2-Cs)-haloalkynyl, (C3-Cio)-cycloalkyl, (C3-Cio)-halocycloalkyl, (C4-C10)cycloalkenyl, (C4-Cio)-halocycloalkenyl, (Ci-Cs)-alkoxy-(Ci-Cs)-alkyl, (Ci-Cs)-haloalkoxy-(CiCs)-alkyl, (Ci-Cs)-alkytthio-(Ci-Cs)-alkyl, (Ci-Cs)-haloalkytthio-(Ci-Cs)-alkyl, (Ci-Cs)-alkoxy(Ci-Cs)-haloalkyl, aryl, aryl-(Ci-Cs)-alkyl, heteroaryl, heteroaryl-(Ci-Cs)-alkyl, (C3-C10)cycloalkyl-(Ci-Cs)-alkyl, (C4-Cio)-cycloalkenyl-(Ci-Cs)-alkyl, COR12, SO2R13, (Ci-Cs)-alkylHNO2S-, (C3-Cio)-cycloalkyl-HN02S-, heterocyclyl, (Ci-Cs)-alkoxycarbonyl-(Ci-Cs)-alkyl, (CiCs)-alkoxycarbonyl, aryl-(Ci-Cs)-alkoxycarbonyl-(Ci-Cs)-alkyl, aryl-(Ci-Cs)-alkoxycarbonyl, heteroaryl-(Ci-Cs)-alkoxycarbonyl, (C2-Cs)-alkenyloxycarbonyl, (C2-Cs)-alkynyloxycarbonyl, heterocyclyl-(Ci-Cs)-alkyl,
R12 represents (Ci-Cs)-alkyl, (C2-Cs)-alkenyl, (C2-Cs)-alkynyl, (Ci-Cs)-cyanoalkyl, (C1-C10)haloalkyl, (C2-Cs)-haloalkenyl, (C2-Cs)-haloalkynyl, (C3-Cio)-cycloalkyl, (C3-C10)halocycloalkyl, (C4-Cio)-cycloalkenyl, (C4-Cio)-halocycloalkenyl, (Ci-Cs)-alkoxy-(Ci-Cs)-alkyl, (Ci-Cs)-alkoxy-(Ci-Cs)-haloalkyl, aryl, aryl-(Ci-Cs)-alkyl, heteroaryl, heteroaryl-(Ci-Cs)-alkyl, (C3-Cio)-cycloalkyl-(Ci-Cs)-alkyl, (C4-Cio)-cycloalkenyl-(Ci-Cs)-alkyl, (Ci-Cs)-alkoxycarbonyl(Ci-Cs)-alkyl, (C2-Cs)-alkenyloxycarbonyl-(Ci-Cs)-alkyl, aryl-(Ci-Cs)-alkoxycarbonyl-(Ci-Cs)alkyl, hydroxycarbonyl-(Ci-Cs)-alkyl, heterocyclyl, heterocyclyl-(Ci-Cs)-alkyl,
R13 represents (Ci-Cs)-alkyl, (C2-Cs)-alkenyl, (C2-Cs)-alkynyl, (Ci-Cs)-cyanoalkyl, (C1-C10)haloalkyl, (C2-Cs)-haloalkenyl, (C2-Cs)-haloalkynyl, (C3-Cio)-cycloalkyl, (C3-C10)halocycloalkyl, (C4-Cio)-cycloalkenyl, (C4-Cio)-halocycloalkenyl, (Ci-Cs)-alkoxy-(Ci-Cs)-alkyl, (Ci-Cs)-alkoxy-(Ci-Cs)-haloalkyl, aryl, aryl-(Ci-Cs)-alkyl, heteroaryl, heteroaryl-(Ci-Cs)-alkyl,
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W represents oxygen or sulfur, where the cyclic structural elements (in particular the structural elements aryl, cycloalkyl, cycloalkenyl, heteroaryl and heterocyclyl) of the radicals mentioned in R1, R3, R4, R5, R6, R7, R10, R11, R12 and R13, respectively, are unsubstituted or substituted by one or more radicals selected from the group consisting of halogen, nitro, hydroxy, cyano, NR10Rn, (Ci-C4)-alkyl, (Ci-C4)-haloalkyl, (Ci-C4)-alkoxy, (C1-C4)haloalkoxy, (Ci-C4)-alkyltitio, (Ci-C4)-alkylsulfoxy, (Ci-C4)-alkylsulfone, (Ci-C4)-haloalkyltitio, (CiC4)-haloalkylsulfoxy, (Ci-C4)-haloalkylsulfone, (Ci-C4)-alkoxycarbonyl, (Ci-C4)-haloalkoxycarbonyl, (Ci-C4)-alkylcarboxy, (C3-C6)-cycloalkyl, (C3-C6)-cycloalkyl-(Ci-C6)-alkyl, (Ci-C4)-alkoxycarbonyl(Ci-C4)-alkyl, hydroxycarbonyl, hydroxycarbonyl-(Ci-C4)-alkyl, R10RnN-carbonyl, and where the structural elements cycloalkyl, cycloalkenyl and heterocyclyl have n oxo groups, where n = 0, 1 or 2.
The compounds of the general formula (I) can form salts by addition of a suitable inorganic or organic acid, for example mineral acids, for example HC1, HBr, H2SO4, H3PO4 or HNO3, or organic acids, for example carboxylic acids such as formic acid, acetic acid, propionic acid, oxalic acid, lactic acid or salicylic acid or sulfonic acids, for example p-toluenesulfonic acid, onto a basic group, for example amino, alkylamino, dialkylamino, piperidino, morpholino or pyridino. In such a case, these salts will comprise the conjugated base of the acid as the anion. Suitable substituents in deprotonated form, for example sulfonic acids, particular sulfonamides or carboxylic acids, are capable of forming internal salts with groups, such as amino groups, which are themselves protonatable. Salts may also be formed by action of a base on compounds of the general formula (I). Suitable bases are, for example, organic amines such as trialkylamines, morpholine, piperidine and pyridine, and the hydroxides, carbonates and bicarbonates of ammonium, alkali metals or alkaline earth metals, especially sodium hydroxide, potassium hydroxide, sodium carbonate, potassium carbonate, sodium bicarbonate and potassium bicarbonate. These salts are compounds in which the acidic hydrogen is replaced by an agriculturally suitable cation, for example metal salts, especially alkali metal salts or alkaline earth metal salts, in particular sodium and potassium salts, or else ammonium salts, salts with organic amines or quaternary ammonium salts, for example with cations of the formula [NRaRbRcRd]+ in which Ra to Rd are each independently an organic radical, especially alkyl, aryl, arylalkyl or alkylaryl. Also suitable are alkylsulfonium and alkylsulfoxonium salts, such as (Ci-C4)-trialkylsulfonium and (C1-C4)trialkylsulfoxonium salts.
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The substituted heteroarylpyrrolones of the formula (I) according to the invention can, depending on external conditions such as pH, solvent and temperature, be present in various tautomeric structures, all of which are embraced by the formula (I).
The compounds of the formula (I) used in accordance with the invention and salts thereof are referred to hereinafter as compounds of the general formula (I).
The invention preferably provides compounds of the general formula (I) in which
Q represents the groups Q-l to Q-29
n s' 4/ \ 7 4/ X 7
R4 R R R R R R7
Q-1 Q-2 Q-3 Q-4 Q-5
n yr o'V- ,)=N N 4/ X 7 R7 R4
R4 R R R r4/ R7
Q-6 Q-7 Q-8 Q-9 Q-10
Λ-N 4/ \ 7 R5 4/ X 7 R7 T-Τ' 4' '5 r4 Tf 5/ \ 7
R4 R R R R R R R R
Q-11 Q-12 Q-13 Q-14 „4 Q-15
aLa4 'AfeN 4 Q R N—N V N O
Q-16 Q-17 Q-18 Q-19 Q-20
Figure AU2017379281A1_D0005
Q-21 Q-22 Q-23 Q-25
Figure AU2017379281A1_D0006
Q-26 Q-27 Q-28 Q-29
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A1, A2, A3, A4 are identical or different and independently of one another represent N (nitrogen) or the moiety C-R8, but there are never more than two adjacent nitrogen atoms, and where R8 in the moiety C-R8 in each case has identical or different meanings according to the definition below,
X and Y independently of one another represent C-H or the moiety C-R1, where
X represents C-H if Y represents the moiety C-R1 and
X represents the moiety C-R1 if Y represents C-H,
R1 represents halogen, (Ci-C7)-alkyl, (Ci-C7)-haloalkyl, (Ci-C7)-hydroxyalkyl, (Ci-C7)-alkoxyalkyl, (Ci-C7)-alkoxy, (Ci-C7)-haloalkoxy, (Ci-C7)-alkylthio, (Ci-C7)-haloalkylthio, aryl, heteroaryl, aryloxy, heteroaryloxy, heterocyclyl, (C3-Cio)-cycloalkyl, (C3-Cio)-cycloalkyl-(Ci-C7)-alkyl, (C3-C7)-halocycloalkyl, (C3-C7)-halocycloalkyl-(Ci-C7)-alkyl, (Ci-C7)-alkylcarbonyl, (C2-C7)alkenyl, (C2-C7)-alkynyl, tris-[(Ci-C7)-alkyl]silyl-(C2-C7)-alkynyl, NR10Rn,
R3 represents hydroxy, hydrothio, halogen, NR10Rn, (Ci-C7)-alkoxy, (C3-Cio)-cycloalkyl-(Ci-C7)alkoxy, aryl-(Ci-C7)-alkoxy, (Ci-C7)-alkoxy-(Ci-C7)-alkoxy, arylcarbonyloxy, (C1-C7)alkylcarbonyloxy, aryl-(Ci-C7)-alkylcarbonyloxy, heteroarylcarbonyloxy, (C3-C10)cycloalkylcarbonyloxy, heterocyclylcarbonyloxy, (Ci-C7)-haloalkylcarbonyloxy, (C2-C7)alkenylcarbonyloxy, OC(O)OR12, OC(O)SR12, OC(S)OR12, OC(S)SR12, OSO2R13, OSO2OR12, OCHO,
R4 and R7 independently of one another represent hydrogen, hydrothio, hydroxy, halogen, (Ci-C7)-alkyl, (Ci-C7)-haloalkyl, (C3-Cio)-cycloalkyl, (C3-Cio)-cycloalkyl-(Ci-C7)-alkyl, aryl, heteroaryl, heterocyclyl, aryl-(Ci-C7)-alkyl, heteroaryl-(Ci-C7)-alkyl, heterocyclyl-(Ci-C7)-alkyl, (C2-C7)alkenyl, (C2-C7)-alkynyl, (C2-C7)-haloalkenyl, (C2-C7)-haloalkynyl, (C3-Cio)-halocycloalkyl, (C4-Cio)-cycloalkenyl, (C4-Cio)-halocycloalkenyl, aryl-(C2-C7)-alkenyl, heteroaryl-(C2-C7)alkenyl, heterocyclyl-(C2-C7)-alkenyl, aryl-(C2-C7)-alkynyl, heteroaryl-(C2-C7)-alkynyl, heterocyclyl-(C2-C7)-alkynyl, (C3-Cio)-cycloalkyl-(C2-C7)-alkynyl, arylcarbonyl-(Ci-C7)-alkyl, (Ci-C7)-alkylcarbonyl-(Ci-C7)-alkyl, heteroarylcarbonyl-(Ci-C7)-alkyl, (C3-C10)cycloalkylcarbonyl-(Ci-C7)-alkyl, aryl-(Ci-C7)-alkoxycarbonyl-(Ci-C7)-alkyl, (C1-C7)alkoxycarbonyl-(Ci-C7)-alkyl, (Ci-C7)-alkoxy-(Ci-C7)-alkyl, arylcarbonyloxy-(Ci-C7)-alkyl, heteroarylcarbonyloxy-(Ci-C7)-alkyl, heterocyclylcarbonyloxy-(Ci-C7)-alkyl, (C1-C7)alkylcarbonyloxy-(Ci-C7)-alkyl, (C3-C7)-cycloalkylcarbonyloxy-(Ci-C7)-alkyl, (C1-C7)haloalkoxy-(Ci-C7)-alkyl, aryl-(Ci-C7)-alkoxy-(Ci-C7)-alkyl, heteroaryl-(Ci-C7)-alkoxy-(Ci-C7)alkyl, CHO, C(O)R12, C(O)OR12, C(O)NR10Rn, OR12, SR13, SOR13, SO2R13, NR10Rn, R10RnN(Ci-C7)-alkyl, cyano-(Ci-C7)-alkyl, hydroxycarbonyl-(Ci-C7)-alkyl, hydroxycarbonyl, (C1-C7)haloalkoxy-(Ci-C7)-alkylthio, (Ci-C7)-alkylthio-(Ci-C7)-alkylene, (Ci-C7)-haloalkylthio-(Ci-C7)
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R5 represents hydrogen, formyl, (Ci-C7)-alkyl, (Ci-C7)-haloalkyl, hydroxy-(Ci-C7)- alkyl, hydroxycarbonyl-(Ci-C7)-alkyl, (Ci-C7)-alkoxy-(Ci-C7)-alkyl, (C3-Cio)-cycloalkyl, (C3-C10)halocycloalkyl, aryl, heteroaryl, (C3-Cio)-cycloalkyl-(Ci-C7)-alkyl, heterocyclyl, (C2-C7)alkenyl, (C2-C7)-alkynyl, NR10Rn, aryl-(Ci-C7)-alkyl, heteroaryl-(Ci-C7)-alkyl, heterocyclyl(Ci-C7)-alkyl, (Ci-C7)-cyanoalkyl, C(O)R12, C(O)OR12, C(O)NR10R11, SO2R13, (C1-C7)alkoxycarbonyl-(Ci-C7)-alkyl, (C2-C7)-alkenyloxycarbonyl-(Ci-C7)-alkyl, aryl-(Ci-C7)alkoxycarbonyl-(Ci-C7)-alkyl, heteroaryl-(Ci-C7)-alkoxycarbonyl-(Ci-C7)-alkyl, aryloxycarbonyl-(Ci-C7)-alkyl, arylcarbonyl-(Ci-C7)-alkyl, (Ci-C7)-alkylcarbonyl-(Ci-C7)-alkyl, heteroarylcarbonyl-(Ci-C7)-alkyl, heterocyclylcarbonyl-(Ci-C7)-alkyl, or where R4 and R5 together with the nitrogen atom or carbon atom to which they are respectively attached form a partially saturated ring having a total of 3 to 7 members which is optionally interrupted by one to three heteroatoms from the group consisting of N, O and S and optionally substituted further, if Q represents Q-13, Q-14 or Q-15,
R6 represents hydrogen or (Ci-C7)-alkyl,
R8 represents hydrogen, halogen, cyano, nitro, hydrothio, hydroxy, NR10RH, OR12, SR13, SOR13, SO2R13, thiocyanate, isothiocyanate, formyl, (Ci-C7)-alkyl, (C2-C7)-alkenyl, (C2-C7)-alkynyl, (Ci-Cio)-haloalkyl, (C2-C7)-haloalkenyl, (C2-C7)-haloalkynyl, (C3-Cio)-cycloalkyl, (C3-C10)halocycloalkyl, (C4-Cio)-cycloalkenyl, (C4-Cio)-halocycloalkenyl, pentafluorotiiio, (C1-C7)alkoxy-(Ci-C7)-haloalkyl, (Ci-C7)-haloalkoxy-(Ci-C7)-haloalkyl, (Ci-C7)-haloalkoxy-(Ci-C7)alkyl, aryl, aryl-(Ci-C7)-alkyl, heteroaryl, heteroaryl-(Ci-C7)-alkyl, (C3-C7)-cycloalkyl-(Ci-C7)alkyl, (C4-Cio)-cycloalkenyl-(Ci-C7)-alkyl, heterocyclyl, heterocyclyl-(Ci-C7)-alkyl, (C1-C7)alkoxy-(Ci-C7)-alkyl, (Ci-C7)-alkyltitio-(Ci-C7)-alkyl, (Ci-C7)-haloalkylthio-(Ci-C7)-alkyl, (CiC7)-alkylcarbonyl-(Ci-C7)-alkyl, C(O)OR12, C(O)NR10R11, C(O)R12, -C=NOR12,
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-C=NOH, R10R11N-(Ci-C7)-alkyl, R12O(O)C-(Ci-C7)-alkyl, hydroxycarbonyl, hydroxycarbonyl(Ci-C7)-alkyl, aryl-(Ci-C7)-alkynyl, heteroaryl-(Ci-C7)-alkynyl, heterocyclyl-(Ci-C7)-alkynyl, tris-[(Ci-C7)-alkyl]silyl-(C2-C7)-alkynyl, bis-[(Ci-C7)-alkyl](aryl)silyl-(C2-C7)-alkynyl, bisaryl[(Ci-C7)-alkyl]silyl-(C2-C7)-alkynyl, (C3-C7)-cycloalkyl-(C2-C7)-alkynyl, aryl-(C2-C7)alkenyl, heteroaryl-(C2-C7)-alkenyl, heterocyclyl-(C2-C7)-alkenyl, (C3-C7)-cycloalkyl-(C2-C7)alkenyl, (Ci-C7)-alkoxy-(Ci-C7)-alkoxy-(Ci-C7)-alkyl, (Ci-C7)-alkylaminosulfonylamino, (C3C7)-cycloalkylaminosulfonylamino, diazo, aryldiazo, iris-[(Ci-C7)-alkyl]silyl, bis-[(Ci-C?)alkyl] (aryl)silyl, bis-aryl[(C1-C7)-alky 1]silyl, or where A1 and A2, when each is a group C-R8, together with the atoms to which they are attached form a partially saturated or fully unsaturated 5- to 7-membered ring which is optionally interrupted by heteroatoms from the group consisting of N, O and S and optionally substituted further, or where A2 and A3, when each is a group C-R8, together with the atoms to which they are attached form a partially saturated or fully unsaturated 5- to 7-membered ring which is optionally interrupted by heteroatoms from the group consisting of N, O and S and optionally substituted further, or where A3 and A4, when each is a group C-R8, together with the atoms to which they are attached form a partially saturated or fully unsaturated 5- to 7-membered ring which is optionally interrupted by heteroatoms from the group consisting of N, O and S and optionally substituted further,
R10 and R11 are identical or different and independently of one another represent hydrogen, (C1-C7)alkyl, (C2-C7)-alkenyl, (C2-C7)-alkynyl, (Ci-C7)-cyanoalkyl, (Ci-Cio)-haloalkyl, (C2-C7)haloalkenyl, (C2-C7)-haloalkynyl, (C3-Cio)-cycloalkyl, (C3-Cio)-halocycloalkyl, (C4-C10)cycloalkenyl, (C4-Cio)-halocycloalkenyl, (Ci-C7)-alkoxy-(Ci-C7)-alkyl, (Ci-C7)-haloalkoxy-(CiC7)-alkyl, (Ci-C7)-alkylthio-(Ci-C7)-alkyl, (Ci-C7)-haloalkylthio-(Ci-C7)-alkyl, (Ci-C7)-alkoxy(Ci-C7)-haloalkyl, aryl, aryl-(Ci-C7)-alkyl, heteroaryl, heteroaryl-(Ci-C7)-alkyl, (C3-C10)cycloalkyl-(Ci-C7)-alkyl, (C4-Cio)-cycloalkenyl-(Ci-C7)-alkyl, COR12, SO2R13, (Ci-C7)-alkylHNO2S-, (C3-Cio)-cycloalkyl-HN02S-, heterocyclyl, (Ci-C7)-alkoxycarbonyl-(Ci-C7)-alkyl, (CiC7)-alkoxycarbonyl, aryl-(Ci-C7)-alkoxycarbonyl-(Ci-C7)-alkyl, aryl-(Ci-C7)-alkoxycarbonyl, heteroaryl-(Ci-C7)-alkoxycarbonyl, (C2-C7)-alkenyloxycarbonyl, (C2-C7)-alkynyloxycarbonyl, heterocyclyl-(Ci-C7)-alkyl,
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R12 represents (Ci-C7)-alkyl, (C2-C7)-alkenyl, (C2-C7)-alkynyl, (Ci-C7)-cyanoalkyl, (Ci-Cio)haloalkyl, (C2-C7)-haloalkenyl, (C2-C7)-haloalkynyl, (C3-Cio)-cycloalkyl, (C3-C10)halocycloalkyl, (C4-Cio)-cycloalkenyl, (C4-Cio)-halocycloalkenyl, (Ci-C7)-alkoxy-(Ci-C7)-alkyl, (Ci-C7)-alkoxy-(Ci-C7)-haloalkyl, aryl, aryl-(Ci-C7)-alkyl, heteroaryl, heteroaryl-(Ci-C7)-alkyl, (C3-Cio)-cycloalkyl-(Ci-C7)-alkyl, (C4-Cio)-cycloalkenyl-(Ci-C7)-alkyl, (Ci-C7)-alkoxycarbonyl(Ci-C7)-alkyl, (C2-C7)-alkenyloxycarbonyl-(Ci-C7)-alkyl, aryl-(Ci-C7)-alkoxycarbonyl-(Ci-C7)alkyl, hydroxycarbonyl-(Ci-C7)-alkyl, heterocyclyl, heterocyclyl-(Ci-C7)-alkyl,
R13 represents (Ci-C7)-alkyl, (C2-C7)-alkenyl, (C2-C7)-alkynyl, (Ci-C7)-cyanoalkyl, (C1-C10)haloalkyl, (C2-C7)-haloalkenyl, (C2-C7)-haloalkynyl, (C3-Cio)-cycloalkyl, (C3-C10)halocycloalkyl, (C4-Cio)-cycloalkenyl, (C4-Cio)-halocycloalkenyl, (Ci-C7)-alkoxy-(Ci-C7)-alkyl, (Ci-C7)-alkoxy-(Ci-C7)-haloalkyl, aryl, aryl-(Ci-C7)-alkyl, heteroaryl, heteroaryl-(Ci-C7)-alkyl, heterocyclyl-(Ci-C7)-alkyl, (C3-Cio)-cycloalkyl-(Ci-C7)-alkyl, (C4-Cio)-cycloalkenyl-(Ci-C7)alkyl, NR10Rn, and
W represents oxygen or sulfur.
The invention more preferably provides compounds of the general formula (1) in which
Q represents the moieties Q-1 to Q-29
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4)=N 4/ X 7 4/ X 7 p4
R4 R R R R R R7
Q-1 Q-2 Q-3 Q-4 Q-5
:£r A- ,)=N n 4/ X 7 ύγ
R4 R R R r4/ R7
Q-6 Q-7 Q-8 Q-9 Q-10
,/- n iF 4/ X 7 4/ \ 7 p7 Y-X 4/ '5 p4 ΥΓ 5/ X 7
R R R R R R R R R
Q-11 Q-12 Q-13 Q-14 „4 Q-15
A'A4 'AfeN 4 D4 O R R7-yyN—N 'r5 N Ox '-C
Q-16 Q-17 Q-18 Q-19 Q-20
Figure AU2017379281A1_D0007
Q-21 Q-22
R4' N'R 5 _N N—N 'r5
Q-26 Q-27
Figure AU2017379281A1_D0008
A1, A2, A3, A4 are identical or different and independently of one another represent N (nitrogen) or the moiety C-R8, but there are never more than two adjacent nitrogen atoms, and where R8 in the 5 moiety C-R8 in each case has identical or different meanings according to the definition below,
X and Y independently of one another represent C-H or the moiety C-R1, where
X represents C-H if Y represents the moiety C-R1 and
X represents the moiety C-R1 if Y represents C-H,
R1 represents halogen, (Ci-Cej-alkyl, (Ci-Cej-haloalkyl, (Ci-Cej-hydroxyalkyl, (Ci-Cej-alkoxyalkyl, (Ci-Cej-alkoxy, (Ci-Cej-haloalkoxy, (Ci-Cej-alkylthio, (Ci-Cej-haloalkylthio, aryl, heteroaryl,
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PCT/EP2017/082832 aryloxy, heteroaryloxy, heterocyclyl, (C3-Cio)-cycloalkyl, (C3-Cio)-cycloalkyl-(Ci-C6)-alkyl, (C3-C6)-halocycloalkyl, (C3-C6)-halocycloalkyl-(Ci-C6)-alkyl, (Ci-C6)-alkylcarbonyl, (C2-C6)alkenyl, (C2-C6)-alkynyl, tris-[(Ci-C6)-alkyl]silyl-(C2-C6)-alkynyl, NR10RH,
R3 represents hydroxy, hydrothio, halogen, NR10Rn, (Ci-C6)-alkoxy, (C3-Cio)-cycloalkyl-(Ci-C6)alkoxy, aryl-(Ci-C6)-alkoxy, (Ci-C6)-alkoxy-(Ci-C6)-alkoxy, arylcarbonyloxy, (Ci-Ce)alkylcarbonyloxy, aryl-(Ci-C6)-alkylcarbonyloxy, heteroarylcarbonyloxy, (C3-C10)cycloalkylcarbonyloxy, heterocyclylcarbonyloxy, (Ci-C6)-haloalkylcarbonyloxy, (C2-C6)alkenylcarbonyloxy, OC(O)OR12, OC(O)SR12, OC(S)OR12, OC(S)SR12, OSO2R13, OSO2OR12, OCHO,
R4 and R7 independently of one another represent hydrogen, hydrothio, hydroxy, halogen, (Ci-C6)-alkyl, (Ci-C6)-haloalkyl, (C3-Cio)-cycloalkyl, (C3-Cio)-cycloalkyl-(Ci-C6)-alkyl, aryl, heteroaryl, heterocyclyl, aryl-(Ci-C6)-alkyl, heteroaryl-(Ci-C6)-alkyl, heterocyclyl-(Ci-C6)-alkyl, (C2-C6)alkenyl, (C2-C6)-alkynyl, (C2-C6)-haloalkenyl, (C2-C6)-haloalkynyl, (C3-Cio)-halocycloalkyl, (C4-Cio)-cycloalkenyl, (C4-Cio)-halocycloalkenyl, aryl-(C2-C6)-alkenyl, heteroaryl-(C2-C6)alkenyl, heterocyclyl-(C2-C6)-alkenyl, aryl-(C2-C6)-alkynyl, heteroaryl-(C2-C6)-alkynyl, heterocyclyl-(C2-C6)-alkynyl, (C3-Cio)-cycloalkyl-(C2-C6)-alkynyl, arylcarbonyl-(Ci-C6)-alkyl, (Ci-C6)-alkylcarbonyl-(Ci-C6)-alkyl, heteroarylcarbonyl-(Ci-C6)-alkyl, (C3-C10)cycloalkylcarbonyl-(Ci-C6)-alkyl, aryl-(Ci-C6)-alkoxycarbonyl-(Ci-C6)-alkyl, (Ci-Ce)alkoxycarbonyl-(Ci-C6)-alkyl, (Ci-C6)-alkoxy-(Ci-C6)-alkyl, arylcarbonyloxy-(Ci-C6)-alkyl, heteroarylcarbonyloxy-(Ci-C6)-alkyl, heterocyclylcarbonyloxy-(Ci-C6)-alkyl, (Ci-Ce)alkylcarbonyloxy-(Ci-C6)-alkyl, (C3-C6)-cycloalkylcarbonyloxy-(Ci-C6)-alkyl, (Ci-Ce)haloalkoxy-(Ci-C6)-alkyl, aryl-(Ci-C6)-alkoxy-(Ci-C6)-alkyl, heteroaryl-(Ci-C6)-alkoxy-(Ci-C6)alkyl, CHO, C(O)R12, C(O)OR12, C(O)NR10Rn, OR12, SR13, SOR13, SO2R13, NR10Rn, R10RnN(Ci-C6)-alkyl, cyano-(Ci-C6)-alkyl, hydroxycarbonyl-(Ci-C6)-alkyl, hydroxycarbonyl, (Ci-Ce)haloalkoxy-(Ci-C6)-alkylthio, (Ci-C6)-alkylthio-(Ci-C6)-alkylene, (Ci-C6)-haloalkylthio-(Ci-C6)alkylthio, (Ci-C6)-alkylthio-(Ci-C6)-alkylthio, aminocarbonyl, aminocarbonyl-(Ci-C6)-alkyl, (Ci-C6)-alkylaminocarbonyl-(Ci-C6)-alkyl, (C3-C6)-cycloalkylaminocarbonyl-(Ci-C6)-alkyl, (C2C6)-alkenyloxycarbonyl-(Ci-C6)-alkyl, (C3-C6)-cycloalkyl- (Ci-C6)-alkoxycarbonyl-(Ci-C6)alkyl, cyano, hydroxy-(Ci-C6)-alkyl, (C2-C6)-alkenyloxy-(Ci-C6)-alkyl, or where R4 and R7 together with the carbon atom to which they are respectively attached form a partially saturated ring having a total of 3 to 7 members which is optionally interrupted by one to three heteroatoms from the group consisting of N, O and S and optionally substituted further, if Q represents Q-3, Q-4, Q-8, Q-9, Q-12 or Q-19,
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R5 represents hydrogen, formyl, (Ci-C6)-alkyl, (Ci-C6)-haloalkyl, hydroxy-(Ci-C6)alkyl, hydroxycarbonyl-(Ci-C6)-alkyl, (Ci-C6)-alkoxy-(Ci-C6)-alkyl, (C3-Cio)-cycloalkyl, (C3-C10)halocycloalkyl, aryl, heteroaryl, (C3-Cio)-cycloalkyl-(Ci-C6)-alkyl, heterocyclyl, (C2-C6)alkenyl, (C2-C6)-alkynyl, NR10Rn, aryl-(Ci-C6)-alkyl, heteroaryl-(Ci-C6)-alkyl, heterocyclyl(Ci-Ce)-alkyl, (Ci-Ce)-cyanoalkyl, C(O)R12, C(O)OR12, C(O)NR10R11, SO2R13, (Ci-C6)alkoxycarbonyl-(Ci-C6)-alkyl, (C2-C6)-alkenyloxycarbonyl-(Ci-C6)-alkyl, aryh/Ci-Ce)alkoxycarbonyl-(Ci-C6)-alkyl, heteroaryl-(Ci-C6)-alkoxycarbonyl-(Ci-C6)-alkyl, aryloxycarbonyl-(Ci-C6)-alkyl, arylcarbonyl-(Ci-C6)-alkyl, (Ci-C6)-alkylcarbonyl-(Ci-C6)-alkyl, heteroarylcarbonyl-(Ci-C6)-alkyl, heterocyclylcarbonyl-(Ci-C6)-alkyl, or where R4 and R5 together with the nitrogen atom or carbon atom to which they are respectively attached form a partially saturated ring having a total of 3 to 7 members which is optionally interrupted by one to three heteroatoms from the group consisting of N, O and S and optionally substituted further, if Q represents Q-13, Q-14 or Q-15,
R6 represents hydrogen or (Ci-C6)-alkyl,
R8 represents hydrogen, halogen, cyano, nitro, hydrothio, hydroxy, NR10RH, OR12, SR13, SOR13, SO2R13, thiocyanate, isothiocyanate, formyl, (Ci-C6)-alkyl, (C2-C6)-alkenyl, (C2-C6)-alkynyl, (Ci-Cio)-haloalkyl, (C2-C6)-haloalkenyl, (C2-C6)-haloalkynyl, (C3-Cio)-cycloalkyl, (C3-C10)halocycloalkyl, (C4-Cio)-cycloalkenyl, (C4-Cio)-halocycloalkenyl, pentafluorothio, (Ci-Ce)alkoxy-(Ci-C6)-haloalkyl, (Ci-C6)-haloalkoxy-(Ci-C6)-haloalkyl, (Ci-C6)-haloalkoxy-(Ci-C6)alkyl, aryl, aryl-(Ci-C6)-alkyl, heteroaryl, heteroaryl-(Ci-C6)-alkyl, (C3-C6)-cycloalkyl-(Ci-C6)alkyl, (C4-Cio)-cycloalkenyl-(Ci-C6)-alkyl, heterocyclyl, heterocyclyl-(Ci-C6)-alkyl, (Ci-Ce)alkoxy-(Ci-C6)-alkyl, (Ci-C6)-alkyltitio-(Ci-C6)-alkyl, (Ci-C6)-haloalkyltitio-(Ci-C6)-alkyl, (CiC6)-alkylcarbonyl-(Ci-C6)-alkyl, C(O)OR12, C(O)NR10R11, C(O)R12, -C=NOR12, -C=NOH, R10RnN-(Ci-C6)-alkyl, R12O(O)C-(Ci-C6)-alkyl, hydroxycarbonyl, hydroxycarbonyl(Ci-C6)-alkyl, aryl-(Ci-C6)-alkynyl, heteroaryl-(Ci-C6)-alkynyl, heterocyclyl-(Ci-C6)-alkynyl, tris-[(Ci-C6)-alkyl]silyl-(C2-C6)-alkynyl, bis-[(Ci-C6)-alkyl](aryl)silyl-(C2-C6)-alkynyl, bisaryl[(Ci-C6)-alkyl]silyl-(C2-C6)-alkynyl, (C3-C6)-cycloalkyl-(C2-C6)-alkynyl, aryl-(C2-C6)alkenyl, heteroaryl-(C2-C6)-alkenyl, heterocyclyl-(C2-C6)-alkenyl, (C3-C6)-cycloalkyl-(C2-C6)alkenyl, (Ci-C6)-alkoxy-(Ci-C6)-alkoxy-(Ci-C6)-alkyl, (Ci-C6)-alkylaminosulfonylamino, (C3C6)-cycloalkylaminosulfonylamino, diazo, aryldiazo, tris-[(Ci-C6)-alkyl]silyl, bis-f/Ci-Ce)alkyl] (aryl)silyl, bis-aryl[(C1 -Ce)-alky 1]silyl, or where A1 and A2, when each is a group C-R8, together with the atoms to which they are attached form a partially saturated or fully unsaturated 5- to 7-membered ring which is
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PCT/EP2017/082832 optionally interrupted by heteroatoms from the group consisting of N, O and S and optionally substituted further, or where A2 and A3, when each is a group C-R8, together with the atoms to which they are attached form a partially saturated or fully unsaturated 5- to 7-membered ring which is optionally interrupted by heteroatoms from the group consisting of N, O and S and optionally substituted further, or where A3 and A4, when each is a group C-R8, together with the atoms to which they are attached form a partially saturated or fully unsaturated 5- to 7-membered ring which is optionally interrupted by heteroatoms from the group consisting of N, O and S and optionally substituted further,
R10 and R11 are identical or different and independently of one another represent hydrogen, (Ci-Ce)alkyl, (C2-C6)-alkenyl, (C2-C6)-alkynyl, (Ci-C6)-cyanoalkyl, (Ci-Cio)-haloalkyl, (C2-C6)haloalkenyl, (C2-C6)-haloalkynyl, (C3-Cio)-cycloalkyl, (C3-Cio)-halocycloalkyl, (C4-C10)cycloalkenyl, (C4-Cio)-halocycloalkenyl, (Ci-C6)-alkoxy-(Ci-C6)-alkyl, (Ci-C6)-haloalkoxy-(CiC6)-alkyl, (Ci-C6)-alkyltitio-(Ci-C6)-alkyl, (Ci-C6)-haloalkyltitio-(Ci-C6)-alkyl, (Ci-C6)-alkoxy(Ci-C6)-haloalkyl, aryl, aryl-(Ci-C6)-alkyl, heteroaryl, heteroaryl-(Ci-C6)-alkyl, (C3-C10)cycloalkyl-(Ci-C6)-alkyl, (C4-Cio)-cycloalkenyl-(Ci-C6)-alkyl, COR12, SO2R13, (Ci-C6)-alkylHNO2S-, (C3-Cw)-cycloalkyl-HNO2S-, heterocyclyl, (Ci-C6)-alkoxycarbonyl-(Ci-C6)-alkyl, (CiC6)-alkoxycarbonyl, aryl-(Ci-C6)-alkoxycarbonyl-(Ci-C6)-alkyl, aryl-(Ci-C6)-alkoxycarbonyl, heteroaryl-(Ci-C6)-alkoxycarbonyl, (C2-C6)-alkenyloxycarbonyl, (C2-C6)-alkynyloxycarbonyl, heterocyclyl-(Ci-C6)-alkyl,
R12 represents (Ci-C6)-alkyl, (C2-C6)-alkenyl, (C2-C6)-alkynyl, (Ci-C6)-cyanoalkyl, (C1-C10)haloalkyl, (C2-C6)-haloalkenyl, (C2-C6)-haloalkynyl, (C3-Cio)-cycloalkyl, (C3-C10)halocycloalkyl, (C4-Cio)-cycloalkenyl, (C4-Cio)-halocycloalkenyl, (Ci-C6)-alkoxy-(Ci-C6)-alkyl, (Ci-C6)-alkoxy-(Ci-C6)-haloalkyl, aryl, aryl-(Ci-C6)-alkyl, heteroaryl, heteroaryl-(Ci-C6)-alkyl, (C3-Cio)-cycloalkyl-(Ci-C6)-alkyl, (C4-Cio)-cycloalkenyl-(Ci-C6)-alkyl, (Ci-C6)-alkoxycarbonyl(Ci-C6)-alkyl, (C2-C6)-alkenyloxycarbonyl-(Ci-C6)-alkyl, aryl-(Ci-C6)-alkoxycarbonyl-(Ci-C6)alkyl, hydroxycarbonyl-(Ci-C6)-alkyl, heterocyclyl, heterocyclyl-(Ci-C6)-alkyl,
R13 represents (Ci-C6)-alkyl, (C2-C6)-alkenyl, (C2-C6)-alkynyl, (Ci-C6)-cyanoalkyl, (C1-C10)haloalkyl, (C2-C6)-haloalkenyl, (C2-C6)-haloalkynyl, (C3-Cio)-cycloalkyl, (C3-C10)halocycloalkyl, (C4-Cio)-cycloalkenyl, (C4-Cio)-halocycloalkenyl, (Ci-C6)-alkoxy-(Ci-C6)-alkyl, (Ci-C6)-alkoxy-(Ci-C6)-haloalkyl, aryl, aryl-(Ci-C6)-alkyl, heteroaryl, heteroaryl-(Ci-C6)-alkyl,
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PCT/EP2017/082832 heterocyclyl-(Ci-C6)-alkyl, (C3-Cio)-cycloalkyl-(Ci-C6)-alkyl, (C4-Cio)-cycloalkenyl-(Ci-C6)alkyl, NR10Rn, and
W represents oxygen or sulfur.
The invention very particularly preferably provides compounds of the general formula (1) in which
Q represents the groups Q-l to Q-29
:£r N s' 4/ X 7 4/ X 7
R4 R R R R R R7
Q-1 Q-2 Q-3 Q-4 Q-5
p- o'V- ,)=N 4/ X 7 p7 p4 pp
R4 R R R r4/ R7
Q-6 Q-7 Q-8 Q-9 Q-10
«/-N 4/ \ 7 p5 R-Nz 4/ X 7 R7 yr 4' '5 p4 O' 5/ \ 7
R4 R R R R R R R R
Q-11 Q-12 Q-13 Q-14 „4 Q-15
aLa4 'AfeN 4 q R'—~ R SrV·' N—N 'r5 N oz '-ζ/
Q-16 Q-17 Q-18 Q-19 Q-20
Figure AU2017379281A1_D0009
Q-21 Q-22 Q-23 Q-25
y— n 4/ '5 N—N X 5 _N N—N 5/ .N ΐ-Γ _5/ X 7
R R R R R R
Q-26 Q-27 Q-28 Q-29
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A1, A2, A3, A4 are identical or different and independently of one another represent N (nitrogen) or the moiety C-R8, but there are never more than two adjacent nitrogen atoms, and where R8 in the moiety C-R8 in each case has identical or different meanings according to the definition above,
X and Y independently of one another represent C-H or the moiety C-R1, where
X represents C-H if Y represents the moiety C-R1 and
X represents the moiety C-R1 if Y represents C-H,
R1 represents fluorine, chlorine, bromine, iodine, methyl, ethyl, n-propyl, 1 -methylethyl, n-butyl, 1 methylpropyl, 2-methylpropyl, 1,1-dimethylethyl, n-pentyl, 1-methylbutyl, 2-methylbutyl, 3methylbutyl, 1,1 -dimethylpropyl, 1,2-dimethylpropyl, 2,2-dimethylpropyl, 1 -ethylpropyl, nhexyl, 1-methylpentyl, 2-methylpentyl, 3-methylpentyl, 4-methylpentyl, 1,1-dimethylbutyl, 1,2dimethylbutyl, 1,3-di-methylbutyl, 2,2-dimethylbutyl, 2,3-dimethylbutyl, 3,3-dimethylbutyl, 1ethylbutyl, 2-ethylbutyl, 1,1,2-trimethylpropyl, 1,2,2-trimethylpropyl, 1 -ethyl-1 -methylpropyl,
1- ethyl-2-methylpropyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, spiro[2.2]pent-l-yl, spiro[2.3]hex-l-yl, spiro[2.3]hex-4-yl, 3-spiro[2.3]hex-5-yl, spiro[3.3]hept-l-yl, spiro[3.3]hept-
2- yl, bicyclo[1.1.0]butan-l-yl, bicyclo[1.1.0]butan-2-yl, bicyclo[2.1.0]pentan-l-yl, bicyclo[l. 1.1 ]pentan-l -yl, bicyclo[2.1,0]pentan-2-yl, bicyclo[2.1,0]pentan-5-yl, bicyclo[2.1.1]hexyl, bicyclo[2.2.1]hept-2-yl, bicyclo[2.2.2]octan-2-yl, bicyclo[3.2.1]octan-2-yl, bicyclo[3.2.2]nonan-2-yl, adamantan-l-yl, adamantan-2-yl, 1-methylcyclopropyl, 2methylcyclopropyl, 2,2-dimethylcyclopropyl, 2,3-dimethylcyclopropyl, 1,1’-bi(cyclopropyl)-1yl, l,l'-bi(cyclopropyl)-2-yl, 2'-methyl-l,r-bi(cyclopropyl)-2-yl, 1-cyanocyclopropyl, 2cyanocyclopropyl, 1-methylcyclobutyl, 2-methylcyclobutyl, 3-methylcyclobutyl, 3,3dimethylcyclobut-l-yl, 1-cyanocyclobutyl, 2-cyanocyclobutyl, 3-cyanocyclobutyl, 3,3difluorocyclobut-1-yl, 3-fluorocyclobut-l-yl, 2,2-difluorocycloprop-l-yl, 1-fluorocycloprop-1yl, 2-fluorocycloprop-l-yl, 1-allylcyclopropyl, 1-vinylcyclobutyl, 1-vinylcyclopropyl, 1ethylcyclopropyl, 1-methylcyclohexyl, 2-methylcyclohexyl, 3-methylcyclohexyl, 1methoxycyclohexyl, 2-methoxycyclohexyl, 3-methoxycyclohexyl, trifluoromethyl, pentafluoroethyl, 1,1,2,2-tetrafluoroethyl, heptafluoropropyl, nonafluorobutyl, chlorodifluoromethyl, bromodifluoromethyl, dichlorofluoromethyl, iododifluoromethyl, bromo fluoromethyl, 1 -fluoroethyl, 2-fluoroethyl, fluoromethyl, difluoromethyl, 2,2difluoroethyl, 2,2,2-trifluoroethyl, difluoro-tert-butyl, chloromethyl, bromomethyl, hydroxymethyl, hydroxyethyl, hydroxy-n-propyl, methoxy, ethoxy, n-propyloxy, isopropyloxy, n-butyloxy, tert-butyloxy, methoxymethyl, ethoxymethyl, n-propyloxymethyl, isopropyloxymethyl, methoxyethyl, ethoxyethyl, n-propyloxyethyl, isopropyloxyethyl,
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PCT/EP2017/082832 trifluoromethoxy, difluoromethoxy, pentafluoroethoxy, 2,2,1,1 -tetrafluoroethoxy, 2,2,2trifluoroethoxy, 2,2-difluoroethoxy, methylthio, ethylthio, n-propylthio, isopropylthio, trifluoromethylthio, pentafluoroethylthio, phenyl, 2-fluorophenyl, 3-fluorophenyl, 4fluorophenyl, 2,4-difluorophenyl, 2,5-difluorophenyl, 2,6-difluorophenyl, 2,3-difluorophenyl, 3,4-difluorophenyl, 3,5-difluorophenyl, 2,4,5-trifluorophenyl, 3,4,5-trifluorophenyl, 2chlorophenyl, 3-chlorophenyl, 4-chlorophenyl, 2,4-dichlorophenyl, 2,5-dichlorophenyl, 2,6dichlorophenyl, 2,3-dichlorophenyl, 3,4-dichlorophenyl, 3,5-dichlorophenyl, 2,4,5trichlorophenyl, 3,4,5-trichlorophenyl, 2,4,6-trichlorophenyl, 2-bromophenyl, 3-bromophenyl, 4-bromophenyl, 2-iodophenyl, 3-iodophenyl, 4-iodophenyl, 2-bromo-4-fluorophenyl, 2-bromo-
4- chlorophenyl, 3-bromo-4-fluorophenyl, 3-bromo-4-chlorophenyl, 3-bromo-5-fluorophenyl, 3bromo-5-chlorophenyl, 2-fluoro-4-bromophenyl, 2-chloro-4-bromophenyl, 3-fluoro-4bromophenyl, 3-chloro-4-bromophenyl, 2-chloro-4-fluorophenyl, 3-chloro-4-fluorophenyl, 2fluoro-3-chlorophenyl, 2-fluoro-4-chlorophenyl, 2-fluoro-5-chlorophenyl, 3-fluoro-4chlorophenyl, 3-fluoro-5-chlorophenyl, 2-fluoro-6-chlorophenyl, 2-methylphenyl, 3methylphenyl, 4-methylphenyl, 2,4-dimethylphenyl, 2,5-dimethylphenyl, 2,6-dimethylphenyl,
2.3- dimethylphenyl, 3,4-dimethylphenyl, 3,5-dimethylphenyl, 2,4,5-trimethylphenyl, 3,4,5trimefliylphenyl, 2,4,6-trimethylphenyl, 2-methoxyphenyl, 3-methoxyphenyl, 4-methoxyphenyl,
2.4- dimethoxyphenyl, 2,5-dimethoxyphenyl, 2,6-dimethoxyphenyl, 2,3-dimethoxyphenyl, 3,4dimethoxyphenyl, 3,5-dimethoxyphenyl, 2,4,5-trimethoxyphenyl, 3,4,5-trimethoxyphenyl, 2,4,6-trimethoxyphenyl, 2-trifluoromethoxyphenyl, 3-trifluoromethoxyphenyl, 4trifluoromethoxyphenyl, 2-difluoromethoxyphenyl, 3-difluoromethoxyphenyl, 4difluoromethoxyphenyl, 2-trifluoromethylphenyl, 3-trifluoromethylphenyl, 4trifluoromethylphenyl, 2-difluoromethylphenyl, 3-difluoromethylphenyl, 4difluoromethylphenyl, 3,5-bis(trifluoromethyl)-phenyl, 3-trifluoromethy 1-5-fluorophenyl, 3trifluoromethyl-5-chlorophenyl, 3-methyl-5-fluorophenyl, 3-methyl-5-chlorophenyl, 3-methoxy-
5- fluorophenyl, 3-methoxy-5-chlorophenyl, 3-trifluoromethoxy-5-chlorophenyl, 2ethoxyphenyl, 3-ethoxyphenyl, 4-ethoxyphenyl, 2-methylthiophenyl, 3-methylthiophenyl, 4methylthiophenyl, 2-trifluoromethyhhiophenyl, 3-trifluoromethylthiophenyl, 4trifluoromethylthiophenyl, phenyloxy, p-Clphenyloxy, thiophen-2-yl, thiophen-3-yl, pyridin-2yl, pyridin-3-yl, pyridin-4-yl, furan-2-yl, furan-3-yl, tetrahydrofuran-2-yl, cyclopropylmethyl, cyclobutylmethyl, cyclopentylmethyl, cyclohexylmethyl, methylcarbonyl, ethylcarbonyl, npropylcarbonyl, isopropylcarbonyl, n-butylcarbonyl, tert-butylcarbonyl, ethenyl, 1-propenyl, 2propenyl, 1-methyl-ethenyl, l-butenyl, 2-butenyl, 3-butenyl, 1-methyl-1-propenyl, 2-methyl-lpropenyl, 1-methyl-2-propenyl, 2-methyl-2-propenyl, 1-pentenyl, 2-pentenyl, 3-pentenyl, 4pentenyl, 1-methyl-1-butenyl, 2-methyl-l-butenyl, 3-methyl-l-butenyl, 1-methyl-2-butenyl, 2methyl-2-butenyl, 3-methy 1-2-butenyl, l-methyl-3-butenyl, 2-methyl-3-butenyl, 3-methyl-3butenyl, 1,1-dimethyl-2-propenyl, 1,2-dimethyl-1-propenyl, 1,2-dimethyl-2-propenyl, 1-ethyl-1WO 2018/114596
PCT/EP2017/082832 propenyl, l-ethyl-2-propenyl, 1-hexenyl, 2-hexenyl, 3-hexenyl, 4-hexenyl, 5-hexenyl, l-methyl-
1- pentenyl, 2-methyl-1-pentenyl, 3-methyl-1-pentenyl, 4-methyl-l-pentenyl, l-methyl-2pentenyl, 2-methyl-2-pentenyl, 3-methyl-2-pentenyl, 4-methyl-2-pentenyl, l-methyl-3-pentenyl,
2- methyl-3-pentenyl, 3-methyl-3-pentenyl, 4-methyl-3-pentenyl, l-methyl-4-pentenyl, 2methyl-4-pentenyl, 3-methyl-4-pentenyl, 4-methyl-4-pentenyl, 1,1-dimethyl-2-butenyl, 1,1dimethyl-3-butenyl, 1,2-dimethyl-l-butenyl, 1,2-dimethyl-2-butenyl, l,2-dimethyl-3-butenyl,
1,3-dimethyl-l-butenyl, l,3-dimethyl-2-butenyl, l,3-dimethyl-3-butenyl, 2,2-dimethyl-3butenyl, 2,3-dimethyl-1-butenyl, 2,3-dimethyl-2-butenyl, 2,3-dimethyl-3-butenyl, 3,3-dimethyl-
1- butenyl, 3,3-dimethyl-2-butenyl, 1-ethyl-1-butenyl, l-ethyl-2-butenyl, l-ethyl-3-butenyl, 2ethyl-1-butenyl, 2-ethyl-2-butenyl, 2-ethyl-3-butenyl, 1,1,2-trimethyl-2-propenyl, 1 -ethyl-1 methyl-2-propenyl, l-ethyl-2-methyl-l-propenyl and l-ethyl-2-methyl-2-propenyl, prop-2-en-lyloxy, but-3-en-l-yloxy, pent-4-en-l-yloxy, ethynyl, 1-propynyl, 2-propynyl, l-butynyl, 2butynyl, 3-butynyl, 1-methyl-2-propynyl, 1-pentynyl, 2-pentynyl, 3-pentynyl, 4-pentynyl, 1methyl-2-butynyl, l-methyl-3-butynyl, 2-methyl-3-butynyl, 3-methyl-l-butynyl, 1,1-dimethyl-
2- propynyl, l-ethyl-2-propynyl, 1-hexynyl, 2-hexynyl, 3-hexynyl, 4-hexynyl, 5-hexynyl, 1methyl-2-pentynyl, l-methyl-3-pentynyl, 1-methyl-4-pentynyl, 2-methyl-3-pentynyl, 2-methyl4-pentynyl, 3-methyl-1-pentynyl, 3-methyl-4-pentynyl, 4-methyl-l-pentynyl, 4-methyl-2pentynyl, 1,1-dimethyl-2-butynyl, l,l-dimethyl-3-butynyl, l,2-dimethyl-3-butynyl, 2,2dimethyl-3-butynyl, 3,3-dimethyl-l-butynyl, 1-ethyl-2-butynyl, l-ethyl-3-butynyl, 2-ethyl-3butynyl, 1-ethyl-1-methyl-2-propynyl, 2-(trimethylsilyl)ethyn-l-yl, 2-(triethylsilyl)ethyn-l-yl, 2-(triisopropylsilyl)ethyn-l-yl, amino, dimethylamino, diethylamino, methylamino, ethylamino, cyclopropylamino, n-propylamino, isopropylamino,
R3 represents hydroxy, hydrothio, fluorine, chlorine, bromine, iodine, methoxy, ethoxy, npropyloxy, 1 -methylethoxy, n-butyloxy, 1 -methylpropyloxy, 2-methylpropyloxy, 1,1dimethylethoxy, n-pentyloxy, 1-methylbutyloxy, 2-methylbutyloxy, 3-methylbutyloxy, 1,1dimethylpropyloxy, 1,2-dimethylpropyloxy, 2,2-dimethylpropyloxy, 1 -ethylpropyloxy, nhexyloxy, 1-methylpentyloxy, 2-methylpentyloxy, 3-methylpentyloxy, 4-methylpentyloxy, 1,1dimethylbutyloxy, 1,2-dimethylbutyloxy, 1,3-dimethylbutyloxy, 2,2-dimethylbutyloxy, 2,3dimethylbutyloxy, 3,3-dimethylbutyloxy, 1-ethylbutyloxy, 2-ethylbutyloxy, 1,1,2trimethylpropyloxy, 1,2,2-trimethylpropyloxy, 1 -ethyl-1 -methylpropyloxy, 1 -ethyl-2methylpropyloxy, cyclopropylmethoxy, cyclobutylmethoxy, cyclopentylmethoxy, cyclohexylmethoxy, benzyloxy, p-chlorophenylmethoxy, m-chlorophenylmethoxy, ochlorophenylmethoxy, p-methoxyphenylmethoxy, p-nitrophenylmethoxy, methoxymethoxy, methoxyethoxy, methoxy-n-propyloxy, methoxy-n-butyloxy, ethoxymethoxy, ethoxyethoxy, ethoxy-n-propyloxy, ethoxy-n-butyloxy, n-propyloxymethoxy, isopropyloxymethoxy, methylcarbonyloxy, ethylcarbonyloxy, n-propylcarbonyloxy, 1 -methylethylcarbonyloxy, n
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PCT/EP2017/082832 butylcarbonyloxy, 1 -methylpropylcarbonyloxy, 2-methylpropylcarbonyloxy, 1,1dimethylethylcarbonyloxy, n-pentylcarbonyloxy, 1-methylbutylcarbonyloxy, 2methylbutylcarbonyloxy, 3-methylbutylcarbonyloxy, 1,1-dimethylpropylcarbonyloxy, 1,2dimethylpropylcarbonyloxy, 2,2-dimethylpropylcarbonyloxy, 1-ethylpropylcarbonyloxy, nhexylcarbonyloxy, 1-methylpentylcarbonyloxy, 2-methylpentylcarbonyloxy, 3methylpentylcarbonyloxy, 4-methylpentylcarbonyloxy, 1,1-dimethylbutylcarbonyloxy, 1,2dimethylbutylcarbonyloxy, 1,3-dimethylbutylcarbonyloxy, 2,2-dimethylbutylcarbonyloxy, 2,3dimethylbutylcarbonyloxy, 3,3-dimethylbutylcarbonyloxy, 1-ethylbutylcarbonyloxy, 2ethylbutylcarbonyloxy, 1,1,2-trimethylpropylcarbonyloxy, 1,2,2-trimethylpropylcarbonyloxy, 1ethyl-1-methylpropylcarbonyloxy, 1-ethyl-2-methylpropylcarbonyloxy, phenylcarbonyloxy, pchlorophenylcarbonyloxy, m-chlorophenylcarbonyloxy, o-chlorophenylcarbonyloxy, pfluorophenylcarbonyloxy, m-fluorophenylcarbonyloxy, o-fluorophenylcarbonyloxy, benzylcarbonyloxy, thiophen-2-ylcarbonyloxy, furan-2-ylcarbonyloxy, cyclopropylcarbonyloxy, cyclobutylcarbonyloxy, cyclopentylcarbonyloxy, cyclohexylcarbonyloxy, trifluoromethylcarbonyloxy, difluoromethylcarbonyloxy, methoxycarbonyloxy, ethoxycarbonyloxy, n-propyloxycarbonyloxy, isopropyloxycarbonyloxy, nbutyloxycarbonyloxy, 1,1 -dimethylethyloxycarbonyloxy, 2,2-dimethylpropyloxycarbonyloxy, pyridin-2-ylcarbonyloxy, pyridin-3-ylcarbonyloxy, pyridin-4-ylcarbonyloxy, 4trifluoromethylpyridin-3-ylcarbonyloxy, allylcarbonyloxy, methylsulfonyloxy, ethylsulfonyloxy, n-propylsulfonyloxy, 1 -methylethylsulfonyloxy, cyclopropylsulfonyloxy cyclobutylsulfonyloxy, cyclopentylsulfonyloxy, cyclohexylsulfonyloxy, phenylsulfonyloxy, pchlorophenylsulfonyloxy, m-chlorophenylsulfonyloxy, o-chlorophenylsulfonyloxy, pfluorophenylsulfonyloxy, m-fluorophenylsulfonyloxy, o-fluorophenylsulfonyloxy, pmethoxyphenylsulfonyloxy, m-methoxyphenylsulfonyloxy, o-methoxyphenylsulfonyloxy, pmethylphenylsulfonyloxy, m-methylphenylsulfonyloxy, o-methylphenylsulfonyloxy,
R4 and R7 independently of one another represent hydrogen, fluorine, chlorine, bromine, iodine, hydroxy, hydrothio, methyl, ethyl, n-propyl, 1 -methylethyl, n-butyl, 1 -methylpropyl, 2methylpropyl, 1,1-dimethylethyl, n-pentyl, 1-methylbutyl, 2-methylbutyl, 3-methylbutyl, 1,1dimethylpropyl, 1,2-dimethylpropyl, 2,2-dimethylpropyl, 1 -ethylpropyl, n-hexyl, 1 methylpentyl, 2-methylpentyl, 3-methylpentyl, 4-methylpentyl, 1,1-dimethylbutyl, 1,2dimethylbutyl, 1,3-dimethylbutyl, 2,2-dimethylbutyl, 2,3-dimethylbutyl, 3,3-dimethylbutyl, 1ethylbutyl, 2-ethylbutyl, 1,1,2-trimethylpropyl, 1,2,2-trimethylpropyl, 1 -ethyl-1 -methylpropyl, 1 -ethyl-2-methylpropyl, trifluoromethyl, pentafluoroethyl, 1,1,2,2-tetrafluoroethyl, heptafluoron-propyl, heptafluoroisopropyl, nonafluorobutyl, chlorodifluoromethyl, bromodifluoromethyl, dichlorofluoromethyl, iododifluoromethyl, bromo fluoromethyl, 1 -fluoroethyl, 2-fluoroethyl, fluoromethyl, difluoromethyl, 2,2-difluoroethyl, 2,2,2-trifluoroethyl, difluoro-tert-butyl,
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PCT/EP2017/082832 chloromethyl, bromomethyl, fluoromethyl, 3,3,3-trifluoro-n-propyl, 1-fluoroprop-1-yl, 1trifluoromefliylprop-l-yl, 2-trifluoromethylprop-2-yl, 1-fluoroprop-1-yl, 2-fluoroprop-2-yl, 2chloroprop-2-yl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, 1-methylcycloprop-1-yl, 2methylcycloprop-1-yl, 2,2-dimethylcycloprop-l-yl, 2,3-dimethylcyclopropyl, 1cyanocycloprop-1-yl, 2-cyanocycloprop-l-yl, 1-methylcyclobutyl, 2-methylcyclobutyl, 3methylcyclobutyl, 3,3-dimethylcyclobutyl, 1-cyanocyclobutyl, 2-cyanocyclobutyl, 3cyanocyclobutyl, 1 -allylcyclopropyl, 1 -vinylcyclobutyl, 1 -vinylcyclopropyl, 1 -ethylcyclopropyl, 1-methylcyclohexyl, 2-methylcyclohexyl, 3-methylcyclohexyl, 1-methoxycyclohexyl, 2methoxycyclohexyl, 3-methoxycyclohexyl, spiro[2.2]pent-l-yl, spiro[2.3]hex-l-yl, spiro[2.3]hex-4-yl, 3-spiro[2.3]hex-5-yl, spiro[3.3]hept-l-yl, spiro[3.3]hept-2-yl, bicyclo[ 1.1,0]butan-1 -yl, bicyclo[ 1.1,0]butan-2-yl, bicyclo[2.1,0]pentan-1 -yl, bicyclo[l. 1.1 ]pentan-l-yl, bicyclo[2.1,0]pentan-2-yl, bicyclo[2.1,0]pentan-5-yl, bicyclo[2.1.1]hexyl, bicyclo[2.2.1]hept-2-yl, bicyclo[2.2.2]octan-2-yl, bicyclo[3.2.1]octan-2-yl, bicyclo[3.2.2]nonan-2-yl, adamantan-l-yl, adamantan-2-yl, cyclopropylmethyl, cyclobutylmethyl, cyclopentylmethyl, cyclohexylmethyl, phenyl, 2-fluorophenyl, 3fluorophenyl, 4-fluorophenyl, 2,4-difluorophenyl, 2,5-difluorophenyl, 2,6-difluorophenyl, 2,3difluorophenyl, 3,4-difluorophenyl, 3,5-difluorophenyl, 2,4,5-trifluorophenyl, 3,4,5trifluorophenyl, 2-chlorophenyl, 3-chlorophenyl, 4-chlorophenyl, 2,4-dichlorophenyl, 2,5dichlorophenyl, 2,6-dichlorophenyl, 2,3-dichlorophenyl, 3,4-dichlorophenyl, 3,5dichlorophenyl, 2,4,5-trichlorophenyl, 3,4,5-trichlorophenyl, 2,4,6-trichlorophenyl, 2bromophenyl, 3-bromophenyl, 4-bromophenyl, 2-iodophenyl, 3-iodophenyl, 4-iodophenyl, 2bromo-4-fluorophenyl, 2-bromo-4-chlorophenyl, 3-bromo-4-fluorophenyl, 3-bromo-4chlorophenyl, 3-bromo-5-fluorophenyl, 3-bromo-5-chlorophenyl, 2-fluoro-4-bromophenyl, 2chloro-4-bromophenyl, 3-fluoro-4-bromophenyl, 3-chloro-4-bromophenyl, 2-chloro-4fluorophenyl, 3-chloro-4-fluorophenyl, 2-fluoro-3-chlorophenyl, 2-fluoro-4-chlorophenyl, 2fluoro-5-chlorophenyl, 3-fluoro-4-chlorophenyl, 3-fluoro-5-chlorophenyl, 2-fluoro-6chlorophenyl, 2-methylphenyl, 3-methylphenyl, 4-methylphenyl, 2,4-dimethylphenyl, 2,5dimethylphenyl, 2,6-dimethylphenyl, 2,3-dimethylphenyl, 3,4-dimethylphenyl, 3,5dimethylphenyl, 2,4,5-trimethylphenyl, 3,4,5-trimethylphenyl, 2,4,6-trimethylphenyl, 2methoxyphenyl, 3-methoxyphenyl, 4-methoxyphenyl, 2,4-dimethoxyphenyl, 2,5dimethoxyphenyl, 2,6-dimethoxyphenyl, 2,3-dimethoxyphenyl, 3,4-dimethoxyphenyl, 3,5dimethoxyphenyl, 2,4,5-trimethoxyphenyl, 3,4,5-trimethoxyphenyl, 2,4,6-trimethoxyphenyl, 2trifluoromethoxyphenyl, 3-trifluoromethoxyphenyl, 4-trifluoromethoxyphenyl, 2difluoromethoxyphenyl, 3-difluoromethoxyphenyl, 4-difluoromethoxyphenyl, 2trifluoromethylphenyl, 3-trifluoromethylphenyl, 4-trifluoromethylphenyl, 2difluoromethylphenyl, 3-difluoromethylphenyl, 4-difluoromethylphenyl, 3,5bis(trifluoromefliyl)-phenyl, 3 -trifluoromethyl-5-fluorophenyl, 3 -trifluoromethyl-5 WO 2018/114596
PCT/EP2017/082832 chlorophenyl, 3-methyl-5-fluorophenyl, 3-methyl-5-chlorophenyl, 3-methoxy-5-fluorophenyl,
3- methoxy-5-chlorophenyl, 3-trifluoromethoxy-5-chlorophenyl, 2-ethoxyphenyl, 3ethoxyphenyl, 4-ethoxyphenyl, 2-methylthiophenyl, 3-methylthiophenyl, 4-methyhhiophenyl, 2trifluoromethylthiophenyl, 3-trifluoromethyhhiophenyl, 4-trifluoromethyhhiophenyl, 2ethylphenyl, 3-ethylphenyl, 4-ethylphenyl, 2-methoxycarbonylphenyl, 3methoxycarbonylphenyl, 4-methoxycarbonylphenyl, 2-ethoxycarbonylphenyl, 3ethoxycarbonylphenyl, 4-ethoxycarbonylphenyl, pyridin-2-yl, pyridin-3-yl, pyridin-4-yl, pyrazin-2-yl, pyridazin-3-yl, pyridazin-4-yl, pyrimidin-2-yl, pyrimidin-5-yl, pyrimidin-4-yl, pyridazin-3-ylmethyl, pyridazin-4-ylmethyl, pyrimidin-2-ylmethyl, pyrimidin-5-ylmethyl, pyrimidin-4-ylmethyl, pyrazin-2-ylmethyl, 3-chloro-pyrazin-2-yl, 3-bromo-pyrazin-2-yl, 3methoxy-pyrazin-2-yl, 3-ethoxy-pyrazin-2-yl, 3-trifluoromethylpyrazin-2-yl, 3-cyanopyrazin-2yl, naphth-2-yl, naphth-1-yl, quinolin-4-yl, quinolin-6-yl, quinolin-8-yl, quinolin-2-yl, quinoxalin-2-yl, 2-naphthylmethyl, 1-naphthylmethyl, quinolin-4-ylmethyl, quinolin-6ylmethyl, quinolin-8-ylmethyl, quinolin-2-ylmethyl, quinoxalin-2-ylmethyl, pyrazin-2-ylmethyl,
4- chloropyridin-2-yl, 3-chloropyridin-4-yl, 2-chloropyridin-3-yl, 2-chloropyridin-4-yl, 2chloropyridin-5-yl, 2,6-dichloropyridin-4-yl, 3-chloropyridin-5-yl, 3,5-dichloropyridin-2-yl, 3chloro-5-trifluoromethylpyridin-2-yl, (4-chloropyridin-2-yl)methyl, (3-chloropyridin-4yl)methyl, (2-chloropyridin-3-yl)methyl, (2-chloropyridin-4-yl)methyl, (2-chloropyridin-5yl)methyl, (2,6-dichloropyridin-4-yl)methyl, (3-chloropyridin-5-yl)methyl, (3,5-dichloropyridin2-yl)methyl, thiophen-2-yl, thiophen-3-yl, 5-methylthiophen-2-yl, 5-ethylthiophen-2-yl, 5chlorothiophen-2-yl, 5-bromothiophen-2-yl, 4-methylthiophen-2-yl, 3-methylthiophen-2-yl, 5fluorothiophen-3-yl, 3,5-dimethylthiophen-2-yl, 3-ethylthiophen-2-yl, 4,5-dimethylthiophen-2yl, 3,4-dimethylthiophen-2-yl, 4-chlorothiophen-2-yl, furan-2-yl, 5-methylfuran-2-yl, 5ethylfuran-2-yl, 5-methoxycarbonylfuran-2-yl, 5-chloro furan-2-yl, 5-bromofuran-2-yl, thiophan2-yl, thiophan-3-yl, sulfolan-2-yl, sulfolan-3-yl, tetrahydrothiopyran-4-yl, tetrahydropyran-4-yl, tetrahydrofuran-2-yl, tetrahydrofuran-3-yl, l-(4-methylphenyl)ethyl, l-(3-methylphenyl)ethyl, l-(2-methylphenyl)ethyl, l-(4-chlorophenyl)ethyl, l-(3-chlorophenyl)ethyl, 1-(2chlorophenyl)ethyl, benzyl, (4-fluorophenyl)methyl, (3-fluorophenyl)methyl, (2fluorophenyl)methyl, (2,4-difluorophenyl)methyl, (3,5-difluorophenyl)methyl, (2,5difluorophenyl)methyl, (2,6-difluorophenyl)methyl, (2,4,5-trifluorophenyl)methyl, (2,4,6trifluorophenyl)methyl, (4-chlorophenyl)methyl, (3-chlorophenyl)methyl, (2chlorophenyl)methyl, (2,4-dichlorophenyl)methyl, (3,5-dichlorophenyl)methyl, (2,5dichlorophenyl)methyl, (2,6-dichlorophenyl)methyl, (2,4,5-trichlorophenyl)methyl, (2,4,6trichlorophenyl)methyl, (4-bromophenyl)methyl, (3-bromophenyl)methyl, (2bromophenyl)methyl, (4-iodophenyl)methyl, (3-iodophenyl)methyl, (2-iodophenyl)methyl, (3chloro-5-trifluoromethylpyridin-2-yl)methyl, (2-bromo-4-fluorophenyl)methyl, (2-bromo-4chlorophenyl)methyl, (3-bromo-4-fluorophenyl)methyl, (3-bromo-4-chlorophenyl)methyl, (3
WO 2018/114596
PCT/EP2017/082832 bromo-5-fluorophenyl)methyl, (3-bromo-5-chlorophenyl)methyl, (2-fluoro-4bromophenyl)methyl, (2-chloro-4-bromophenyl)methyl, (3-fluoro-4-bromophenyl)methyl, (3chloro-4-bromophenyl)methyl, (2-chloro-4-fluorophenyl)methyl, (3-chloro-4fluorophenyl)methyl, (2-fluoro-3-chlorophenyl)methyl, (2-fluoro-4-chlorophenyl)methyl, (2fluoro-5-chlorophenyl)methyl, (3-fluoro-4-chlorophenyl)methyl, (3-fluoro-5chlorophenyl)methyl, (2-fluoro-6-chlorophenyl)methyl, 2-phenyleth-l-yl, 3-trifluoromethyl-4chlorophenyl, 3-chloro-4-trifluoromethylphenyl, 2-chloro-4-trifluoromethylphenyl, 3,5difluoropyridin-2-yl, (3,6-dichloropyridin-2-yl)methyl, (4-trifluoromethylphenyl)methyl, (3trifluoromethylphenyl)methyl, (2-trifluoromethylphenyl)methyl, (4trifluoromethoxyphenyl)methyl, (3-trifluoromethoxyp henyl)methyl, (2trifluoromethoxyphenyl)methyl, (4-methoxyphenyl)methyl, (3-methoxyphenyl)methyl, (2methoxyphenyl)methyl, (4-methylphenyl)methyl, (3-methylphenyl)methyl, (2methylphenyl)methyl, (4-cyanophenyl)methyl, (3-cyanophenyl)methyl, (2-cyanophenyl)methyl, (2,4-diethylphenyl)methyl, (3,5-diethylphenyl)methyl, (3,4-dimethylphenyl)methyl, (3,5dimeflioxyphenyl)mefliyl, l-phenyleth-l-yl, l-(o-chlorophenyl)eth-l-yl, l,3-thiazol-2-yl, 4methyl-l,3-thiazol-2-yl, l,3-thiazol-2-yl, ethenyl, 1-propenyl, 2-propenyl, 1-methyl-ethenyl, 1butenyl, 2-butenyl, 3-butenyl, 1-methyl-1-propenyl, 2-methyl-1-propenyl, 1-methyl-2-propenyl,
2- methyl-2-propenyl, 1-pentenyl, 2-pentenyl, 3-pentenyl, 4-pentenyl, 1-methyl-l-butenyl, 2methyl-l-butenyl, 3-methyl-l-butenyl, 1-methyl-2-butenyl, 2-methyl-2-butenyl, 3-methyl-2butenyl, l-methyl-3-butenyl, 2-methyl-3-butenyl, 3-methyl-3-butenyl, 1,1-dimethyl-2-propenyl,
1.2- dimethyl-1-propenyl, 1,2-dimethyl-2-propenyl, 1-ethyl-1-propenyl, 1-ethyl-2-propenyl, 1hexenyl, 2-hexenyl, 3-hexenyl, 4-hexenyl, 5-hexenyl, 1-methyl-1-pentenyl, 2-methyl-1pentenyl, 3-methyl-1-pentenyl, 4-methyl-1-pentenyl, l-methyl-2-pentenyl, 2-methyl-2-pentenyl,
3- methyl-2-pentenyl, 4-methyl-2-pentenyl, l-methyl-3-pentenyl, 2-methyl-3-pentenyl, 3methyl-3-pentenyl, 4-methyl-3-pentenyl, 1-methyl-4-pentenyl, 2-methyl-4-pentenyl, 3-methyl-
4- pentenyl, 4-methyl-4-pentenyl, 1,1-dimethyl-2-butenyl, l,l-dimethyl-3-butenyl, 1,2-dimethyll-butenyl, 1,2-dimethyl-2-butenyl, l,2-dimethyl-3-butenyl, 1,3-dimethyl-l-butenyl, 1,3dimethyl-2-butenyl, l,3-dimethyl-3-butenyl, 2,2-dimethyl-3-butenyl, 2,3-dimethyl-l-butenyl,
2.3- dimethyl-2-butenyl, 2,3-dimethyl-3-butenyl, 3,3-dimethyl-l-butenyl, 3,3-dimethyl-2butenyl, 1-ethyl-l-butenyl, 1-ethyl-2-butenyl, l-ethyl-3-butenyl, 2-ethyl-l-butenyl, 2-ethyl-2butenyl, 2-ethyl-3-butenyl, 1,1,2-trimethyl-2-propenyl, 1-ethyl-l-methyl-2-propenyl, l-ethyl-2methyl-1-propenyl and 1-ethyl-2-methyl-2-propenyl, ethynyl, 1-propynyl, 2-propynyl, 1butynyl, 2-butynyl, 3-butynyl, 1-methyl-2-propynyl, 1-pentynyl, 2-pentynyl, 3-pentynyl, 4pentynyl, 1-methyl-2-butynyl, l-methyl-3-butynyl, 2-methyl-3-butynyl, 3-methyl-l-butynyl, 1,1-dimethyl-2-propynyl, 1-ethyl-2-propynyl, 1-hexynyl, 2-hexynyl, 3-hexynyl, 3,3difluorocyclobut-1-yl, 3-fluorocyclobut-l-yl, 1-fluorocyclobut-1-yl, 2,2-difluorocycloprop-l-yl,
1-fluorocycloprop-1-yl, 2-fluorocycloprop-l-yl, 4-fluorocyclohexyl, 4,4-difluorocyclohexyl,
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PCT/EP2017/082832 methoxycarbonylmethyl, ethoxycarbonylmethyl, n-propyloxycarbonylmethyl, isopropyloxycarbonylmethyl, n-butyloxycarbonylmethyl, tert-butyloxycarbonylmethyl, methoxymethyl, ethoxymethyl, n-propyloxymethyl, isopropyloxymethyl, n-butyloxymethyl, methoxyethyl, ethoxyethyl, n-propyloxyethyl, isopropyloxyethyl, methoxy-n-propyl, methoxyn-butyl, trifluoromethoxymethyl, difluoromethoxymethyl, 2,2-difluoroethoxymethyl, 2,2,2trifluoroethoxymethyl, trifluoromethoxyethyl, difluoromethoxyethyl, 2,2-difluoroethoxyethyl,
2,2,2-trifluoroethoxyethyl, methoxycarbonyl, ethoxycarbonyl, n-propyloxycarbonyl, isopropyloxycarbonyl, n-butyloxycarbonyl, tert-butyloxycarbonyl, allyloxycarbonyl, benzyloxycarbonyl, methylcarbonyl, ethylcarbonyl, n-propylcarbonyl, isopropylcarbonyl, nbutylcarbonyl, tert-butylcarbonyl, phenylcarbonyl, p-chlorophenylcarbonyl, mchlorophenylcarbonyl, o-chlorophenylcarbonyl, p-fluorophenylcarbonyl, mfluorophenylcarbonyl, o-fluorophenylcarbonyl, p-methoxyphenylcarbonyl, mmethoxyphenylcarbonyl, o-methoxyphenylcarbonyl, p-trifluoromethylphenylcarbonyl, mtrifluoromethylphenylcarbonyl, o-trifluoromethylphenylcarbonyl, methoxy, ethoxy, npropyloxy, isopropyloxy, benzyloxy, p-chlorophenylmethoxy, phenyloxy, p-chlorophenyloxy, m-chlorophenyloxy, o-chlorophenyloxy, p-fluorophenyloxy, m-fluorophenyloxy, ofluorophenyloxy, p-methoxyphenyloxy, m-methoxyphenyloxy, o-methoxyphenyloxy, ptrifluoromethylphenyloxy, m-trifluoromethylphenyloxy, o-trifluoromethylphenyloxy, methylaminocarbonyl, ethylaminocarbonyl, n-propylaminocarbonyl, isopropylaminocarbonyl, cyclopropylaminocarbonyl, cyclobutylaminocarbonyl, cyclopentylaminocarbonyl, cyclohexylaminocarbonyl, cyclopropylmethylaminocarbonyl, cyclobutylmethylaminocarbonyl, cyclopentylmethylaminocarbonyl, cyclohexylmethylaminocarbonyl, dimethylaminocarbonyl, diethylaminocarbonyl, benzylmethylaminocarbonyl, methylamino, dimethylamino, ethylamino, diethylamino, n-propylamino, isopropylamino, cyclopropylamino, cyclobutylamino, cyclopentylamino, cyclohexylamino, benzylamino, cyanomethyl, cyanoethyl, 3-cyanoprop-1-yl, 2-cyanoprop-1-yl, 1-cyanoprop-1-yl, 2-cyanoprop-2-yl, 2-cyano-1,1-dimethyleth-1-yl, 1(cyanomethyl)-1 -methylprop-1 -yl, hydroxycarbonyl, hydroxycarbonylmethyl, hydroxycarbonylethyl, CHO, methoxyethylthio, ethoxyethylthio, trifluoromethoxyethylthio, pentafluoroethoxyethylthio, methylthioethylthio, ethylthioethylthio, trifluoromethylthioethylthio, pentafluorothioethylthio, benzylthio, p-chlorophenylmethylthio, mchlorophenylmethylthio, o-chlorophenylmethylthio, p-fluorophenylmethylthio, mfluorophenylmethylthio, o-fluorophenylmethylthio, methylthio, ethylthio, n-propylthio, isopropylthio, n-butylthio, tert-butylthio, cyclobutylthio, cyclopentylthio, cyclohexylthio, phenylthio, pyrid-2-yhhio, pyrid-3-ylthio, pyrid-4-ylthio, p-chlorophenylthio, mchlorophenylthio, o-chlorophenylthio, p-fluorophenylthio, m-fluorophenylthio, ofluorophenylthio, p-methoxyphenylthio, m-methoxyphenylthio, o-methoxyphenylthio, pmethylphenylthio, m-methylphenylthio, o-methylphenylthio, methylsulfonyl, ethylsulfonyl, n
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PCT/EP2017/082832 propylsulfonyl, 1 -methylethylsulfonyl, cyclopropylsulfonyl, cyclobutylsulfonyl, cyclopentylsulfonyl, cyclohexylsulfonyl, phenylsulfonyloxy, p-chlorophenylsulfonyl, mchlorophenylsulfonyl, o-chlorophenylsulfonyl, p-fluorophenylsulfonyl, m-fluorophenylsulfonyl, o-fluorophenylsulfonyl, p-methoxyphenylsulfonyl, m-methoxyphenylsulfonyl, omethoxyphenylsulfonyl, p-methylphenylsulfonyl, m-methylphenylsulfonyl, omethylphenylsulfonyl, 2-methoxyprop-2-yl, 2-ethoxyprop-2-yl, 2-n-propyloxyprop-2-yl, 2-nbutyloxyprop-2-yl, 2-benzyloxyprop-2-yl, 2-phenylethyloxyprop-2-yl, 2trifluoromethyloxyprop-2-yl, 2-difluoromethyloxyprop-2-yl, 2,2,2-trifluoroethyloxyprop-2-yl,
2,2-difluoroethyloxyprop-2-yl, 2-(4-chlorophenylmethoxy)prop-2-yl, 2-(4fluorophenylmethoxy)prop-2-yl, 2-(4-bromophenylmethoxy)prop-2-yl, 2-(4trifluoromethylphenylmethoxy)prop-2-yl, 2-(4-methylphenylmethoxy)prop-2-yl, 2-(3chlorophenylmethoxy)prop-2-yl, 2-(3-fluorophenylmethoxy)prop-2-yl, 2-(3bromophenylmethoxy)prop-2-yl, 2-(3-trifluoromethylphenylmethoxy)prop-2-yl, 2-(3methylphenylmethoxy)prop-2-yl, 2-(2-chlorophenylmethoxy)prop-2-yl, 2-(2fluorophenylmethoxy)prop-2-yl, 2-(2-bromophenylmethoxy)prop-2-yl, 2-(2trifluoromethylphenylmethoxy)prop-2-yl, 2-(2-methylphenylmethoxy)prop-2-yl, 2(methoxymethyl)prop-2-yl, 2-(ethoxymethyl)prop-2-yl, 2-methoxycarbonylprop-2-yl, 2ethoxycarbonylprop-2-yl, 2-hydroxycarbonylprop-2-yl, 2-aminocarbonylprop-2-yl, aminocarbonyl, aminocarbonylmethyl, aminocarbonylethyl, cyano, hydroxymethyl, hydroxyethyl, 2-hydroxyprop-2-yl, allyloxymethyl, 2-allyloxyethyl, 2-allyloxyprop-2-yl, or where R4 and R7 together with the carbon atom to which they are respectively attached form a partially saturated ring having a total of 3 to 7 members which is optionally interrupted by one to three heteroatoms from the group consisting of N, O and S and optionally substituted further, if Q represents Q-3, Q-4, Q-8, Q-9, Q-12 or Q-19,
R5 represents hydrogen, formyl, methyl, ethyl, n-propyl, 1 -methylethyl, n-butyl, 1 -methylpropyl, 2methylpropyl, 1,1-dimethylethyl, n-pentyl, 1-methylbutyl, 2-methylbutyl, 3-methylbutyl, 1,1dimethylpropyl, 1,2-dimethylpropyl, 2,2-dimethylpropyl, 1 -ethylpropyl, n-hexyl, 1 methylpentyl, 2-methylpentyl, 3-methylpentyl, 4-methylpentyl, 1,1-dimethylbutyl, 1,2dimethylbutyl, 1,3-dimethylbutyl, 2,2-dimethylbutyl, 2,3-dimethylbutyl, 3,3-dimethylbutyl, 1ethylbutyl, 2-ethylbutyl, 1,1,2-trimethylpropyl, 1,2,2-trimethylpropyl, 1 -ethyl-1 -methylpropyl, 1-ethyl-2-methylpropyl, 2,2-difluoroethyl, 2,2,2-trifluoroethyl, 3,3,3-trifluoro-n-propyl, methoxymethyl, ethoxymethyl, methoxyethyl, ethoxyethyl, methoxy-n-propyl, methoxy-n-butyl, ethoxy-n-propyl, ethoxy-n-butyl, hydroxyethyl, hydroxy-n-propyl, hydroxycarbonylmethyl, hydroxycarbonylethyl, hydroxycarbonyl-n-propyl, methoxycarbonylmethyl, ethoxycarbonylmethyl, n-propyloxycarbonylmethyl, isopropyloxycarbonylmethyl, tert
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PCT/EP2017/082832 butyloxycarbonylmethyl, methoxy carbonylethyl, ethoxycarbonylethyl, npropyloxycarbonylethyl, isopropyloxycarbonylethyl, tert-butyloxycarbonylethyl, methoxycarbonyl-n-propyl, ethoxycarbonyl-n-propyl, benzyloxycarbonylmethyl, benzyloxycarbonylethyl, allyloxycarbonylmethyl, allyloxycarbonylethyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, 1-methylcycloprop-1-yl, 2-methylcycloprop-l-yl, 2,2dimethylcycloprop-l-yl, 2,3-dimethylcyclopropyl, 1-cyanopropyl, 2-cyanopropyl, 1methylcyclobutyl, 2-methylcyclobutyl, 3-methylcyclobutyl, 3,3-dimethylcyclobutyl, 1cyanocyclobutyl, 2-cyanocyclobutyl, 3-cyanocyclobutyl, 1-allylcyclopropyl, 1-vinylcyclobutyl, 1-vinylcyclopropyl, 1-ethylcyclopropyl, 1-methylcyclohexyl, 2-methylcyclohexyl, 3methylcyclohexyl, 1-methoxycyclohexyl, 2-methoxycyclohexyl, 3-methoxycyclohexyl, cyclopropylmethyl, cyclobutylmethyl, cyclopentylmethyl, cyclohexylmethyl, cyanomethyl, 2cyanoeth-1 -yl, 1 -cyanoeth-1 -yl, cyano-n-propyl, methoxycarbonyl, ethoxycarbonyl, tertbutyloxycarbonyl, benzyloxycarbonyl, n-butyloxycarbonyl, allyloxycarbonyl, methylcarbonyl, ethylcarbonyl, n-propylcarbonyl, isopropylcarbonyl, n-butylcarbonyl, tert-butylcarbonyl, phenylcarbonyl, p-chlorophenylcarbonyl, m-chlorophenylcarbonyl, o-chlorophenylcarbonyl, pfluorophenylcarbonyl, m-fluorophenylcarbonyl, o-fluorophenylcarbonyl, pmethoxyphenylcarbonyl, m-methoxyphenylcarbonyl, o-methoxyphenylcarbonyl, ptrifluoromethylphenylcarbonyl, m-trifluoromethylphenylcarbonyl, otrifluoromethylphenylcarbonyl, methylaminocarbonyl, ethylaminocarbonyl, isopropylaminocarbonyl, n-propylaminocarbonyl, phenylaminocarbonyl, pClphenylaminocarbonyl, m-Clphenylaminocarbonyl, o-Clphenylaminocarbonyl, cyclopropylaminocarbonyl, cyclobutylaminocarbonyl, cyclopentylaminocarbonyl, cyclohexylaminocarbonyl, cyclopropylmethylaminocarbonyl, cyclobutylmethylaminocarbonyl, cyclopentylmethylaminocarbonyl, cyclohexylmethylaminocarbonyl, dimethylaminocarbonyl, diethylaminocarbonyl, benzyl(methyl)aminocarbonyl, prop-2-en-l-yl, prop-2-yn-1-yl, 1fluorocycloprop-1-yl, 2-fluorocycloprop-l-yl, 2,2-difluorocycloprop-l-yl, 3,3-difluorocyclobut1-yl, phenyl, 2-fluorophenyl, 3-fluorophenyl, 4-fluorophenyl, 2,4-difluorophenyl, 2,5difluorophenyl, 2,6-difluorophenyl, 2,3-difluorophenyl, 3,4-difluorophenyl, 3,5-difluorophenyl, 2,4,5-trifluorophenyl, 3,4,5-trifluorophenyl, 2-chlorophenyl, 3-chlorophenyl, 4-chlorophenyl,
2,4-dichlorophenyl, 2,5-dichlorophenyl, 2,6-dichlorophenyl, 2,3-dichlorophenyl, 3,4dichlorophenyl, 3,5-dichlorophenyl, 2,4,5-trichlorophenyl, 3,4,5-trichlorophenyl, 2,4,6trichlorophenyl, 2-bromophenyl, 3-bromophenyl, 4-bromophenyl, 2-iodophenyl, 3-iodophenyl, 4-iodophenyl, 2-bromo-4-fluorophenyl, 2-bromo-4-chlorophenyl, 3-bromo-4-fluorophenyl, 3bromo-4-chlorophenyl, 3-bromo-5-fluorophenyl, 3-bromo-5-chlorophenyl, 2-fluoro-4bromophenyl, 2-chloro-4-bromophenyl, 3-fluoro-4-bromophenyl, 3-chloro-4-bromophenyl, 2chloro-4-fluorophenyl, 3-chloro-4-fluorophenyl, 2-fluoro-3-chlorophenyl, 2-fluoro-4chlorophenyl, 2-fluoro-5-chlorophenyl, 3-fluoro-4-chlorophenyl, 3-fluoro-5-chlorophenyl, 2WO 2018/114596
PCT/EP2017/082832 fluoro-6-chlorophenyl, 2-methylphenyl, 3-methylphenyl, 4-methylphenyl, 2,4-dimethylphenyl,
2,5-dimethylphenyl, 2,6-dimethylphenyl, 2,3-dimethylphenyl, 3,4-dimethylphenyl, 3,5dimethylphenyl, 2,4,5-trimethylphenyl, 3,4,5-trimethylphenyl, 2,4,6-trimethylphenyl, 2methoxyphenyl, 3-methoxyphenyl, 4-methoxyphenyl, 2,4-dimethoxyphenyl, 2,5dimethoxyphenyl, 2,6-dimethoxyphenyl, 2,3-dimethoxyphenyl, 3,4-dimethoxyphenyl, 3,5dimethoxyphenyl, 2,4,5-trimethoxyphenyl, 3,4,5-trimethoxyphenyl, 2,4,6-trimethoxyphenyl, 2trifluoromethoxyphenyl, 3-trifluoromethoxyphenyl, 4-trifluoromethoxyphenyl, 2difluoromethoxyphenyl, 3-difluoromethoxyphenyl, 4-difluoromethoxyphenyl, 2trifluoromethylphenyl, 3-trifluoromethylphenyl, 4-trifluoromethylphenyl, 2difluoromethylphenyl, 3-difluoromethylphenyl, 4-difluoromethylphenyl, 3,5bis(trifluoromefliyl)-phenyl, 3 -trifluoromethyl-5-fluorophenyl, 3 -trifluoromethyl-5 chlorophenyl, 3-methyl-5-fluorophenyl, 3-methyl-5-chlorophenyl, 3-methoxy-5-fluorophenyl, 3methoxy-5-chlorophenyl, 3-trifluoromethoxy-5-chlorophenyl, 2-ethoxyphenyl, 3-ethoxyphenyl, 4-ethoxyphenyl, 2-methylthiophenyl, 3-methylthiophenyl, 4-methylthiophenyl, 2trifluoromethylthiophenyl, 3 -trifluoromethylthiophenyl, 4-trifluoromethyhhiophenyl, methoxymethyl, 2-ethylphenyl, 3-ethylphenyl, 4-ethylphenyl, 2-methoxycarbonylphenyl, 3methoxycarbonylphenyl, 4-methoxycarbonylphenyl, 2-ethoxycarbonylphenyl, 3ethoxycarbonylphenyl, 4-ethoxycarbonylphenyl, pyridin-2-yl, pyridin-3-yl, pyridin-4-yl, pyrazin-2-yl, pyridazin-3-yl, pyridazin-4-yl, pyrimidin-2-yl, pyrimidin-5-yl, pyrimidin-4-yl, pyridazin-3-ylmethyl, pyridazin-4-ylmethyl, pyrimidin-2-ylmethyl, pyrimidin-5-ylmethyl, pyrimidin-4-ylmethyl, pyrazin-2-ylmethyl, 3-chloro-pyrazin-2-yl, 3-bromo-pyrazin-2-yl, 3methoxy-pyrazin-2-yl, 3-ethoxy-pyrazin-2-yl, 3-trifluoromethylpyrazin-2-yl, 3-cyanopyrazin-2yl, naphth-2-yl, naphth-1-yl, quinolin-4-yl, quinolin-6-yl, quinolin-8-yl, quinolin-2-yl, quinoxalin-2-yl, 2-naphthylmethyl, 1-naphthylmethyl, quinolin-4-ylmethyl, quinolin-6ylmethyl, quinolin-8-ylmethyl, quinolin-2-ylmethyl, quinoxalin-2-ylmethyl, pyrazin-2-ylmethyl, 4-chloropyridin-2-yl, 3-chloropyridin-4-yl, 2-chloropyridin-3-yl, 2-chloropyridin-4-yl, 2chloropyridin-5-yl, 2,6-dichloropyridin-4-yl, 3-chloropyridin-5-yl, 3,5-dichloropyridin-2-yl, 3chloro-5-trifluoromethylpyridin-2-yl, (4-chloropyridin-2-yl)methyl, (3-chloropyridin-4yl)methyl, (2-chloropyridin-3-yl)methyl, (2-chloropyridin-4-yl)methyl, (2-chloropyridin-5yl)methyl, (2,6-dichloropyridin-4-yl)methyl, (3-chloropyridin-5-yl)methyl, (3,5-dichloropyridin-
2-yl)methyl, thiophen-2-yl, thiophen-3-yl, 5-methylthiophen-2-yl, 5-ethylthiophen-2-yl, 5chlorothiophen-2-yl, 5-bromothiophen-2-yl, 4-methylthiophen-2-yl, 3-methylthiophen-2-yl, 5fluorothiophen-3-yl, 3,5-dimethylthiophen-2-yl, 3-ethylthiophen-2-yl, 4,5-dimethylthiophen-2yl, 3,4-dimethylthiophen-2-yl, 4-chlorothiophen-2-yl, furan-2-yl, 5-methylfuran-2-yl, 5ethylfuran-2-yl, 5-methoxycarbonylfuran-2-yl, 5-chloro furan-2-yl, 5-bromofuran-2-yl, thiophan2-yl, thiophan-3-yl, sulfolan-2-yl, sulfolan-3-yl, benzyl, (4-fluorophenyl)methyl, (3fluorophenyl)mefliyl, (2-fluorophenyl)methyl, (2,4-difluorophenyl)methyl, (3,5
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PCT/EP2017/082832 difluorophenyl)methyl, (2,5-difluorophenyl)methyl, (2,6-difluorophenyl)methyl, (2,4,5trifluorophenyl)methyl, (2,4,6-trifluorophenyl)methyl, (4-chlorophenyl)methyl, (3chlorophenyl)methyl, (2-chlorophenyl)methyl, (2,4-dichlorophenyl)methyl, (3,5dichlorophenyl)methyl, (2,5-dichlorophenyl)methyl, (2,6-dichlorophenyl)methyl, (2,4,5trichlorophenyl)methyl, (2,4,6-trichlorophenyl)methyl, (4-bromophenyl)methyl, (3bromophenyl)methyl, (2-bromophenyl)methyl, (4-iodophenyl)methyl, (3-iodophenyl)methyl, (2iodophenyl)methyl, (3-chloro-5-trifluoromethylpyridin-2-yl)methyl, (2-bromo-4fluorophenyl)methyl, (2-bromo-4-chlorophenyl)methyl, (3-bromo-4-fluorophenyl)methyl, (3bromo-4-chlorophenyl)methyl, (3-bromo-5-fluorophenyl)methyl, (3-bromo-5chlorophenyl)methyl, (2-fluoro-4-bromophenyl)methyl, (2-chloro-4-bromophenyl)methyl, (3fluoro-4-bromophenyl)methyl, (3-chloro-4-bromophenyl)methyl, (2-chloro-4fluorophenyl)methyl, (3-chloro-4-fluorophenyl)methyl, (2-fluoro-3-chlorophenyl)methyl, (2fluoro-4-chlorophenyl)methyl, (2-fluoro-5-chlorophenyl)methyl, (3-fluoro-4chlorophenyl)methyl, (3-fluoro-5-chlorophenyl)methyl, (2-fluoro-6-chlorophenyl)methyl, phenylethyl, 3-trifluoromethyl-4-chlorophenyl, 3-chloro-4-trifluoromethylphenyl, 2-chloro-4trifluoromethylphenyl, 3,5-difluoropyridin-2-yl, (3,6-dichloropyridin-2-yl)methyl, (4trifluoromethylphenyl)methyl, (3-trifluoromethylphenyl)methyl, (2trifluoromethylphenyl)methyl, (4-trifluoromethoxyphenyl)methyl, (3trifluoromethoxyphenyl)methyl, (2-trifluoromethoxyphenyl)methyl, (4-methoxyphenyl)methyl, (3-methoxyphenyl)methyl, (2-methoxyphenyl)methyl, (4-methylphenyl)methyl, (3methylphenyl)methyl, (2-methylphenyl)methyl, (4-cyanophenyl)methyl, (3cyanophenyl)methyl, (2-cyanophenyl)methyl, (2,4-diethylphenyl)methyl, (3,5diethylphenyl)methyl, (3,4-dimethylphenyl)methyl, (3,5-dimethoxyphenyl)methyl, l-phenyleth1-yl, methylsulfonyl, ethylsulfonyl, n-propylsulfonyl, 1-methylethylsulfonyl, cyclopropylsulfonyl, cyclobutylsulfonyl, cyclopentylsulfonyl, cyclohexylsulfonyl, phenylsulfonyloxy, p-chlorophenylsulfonyl, m-chlorophenylsulfonyl, o-chlorophenylsulfonyl, pfluorophenylsulfonyl, m-fluorophenylsulfonyl, o-fluorophenylsulfonyl, pmethoxyphenylsulfonyl, m-methoxyphenylsulfonyl, o-methoxyphenylsulfonyl, pmethylphenylsulfonyl, m-methylphenylsulfonyl, o-methylphenylsulfonyl, phenylcarbonylmethyl, p-chlorophenylcarbonylmethyl, m-chlorophenylcarbonylmethyl, ochlorophenylcarbonylmethyl, p-fluorophenylcarbonylmethyl, m-fluorophenylcarbonylmethyl, ofluorophenylcarbonylmethyl, methylcarbonylmethyl, ethylcarbonylmethyl, npropylcarbonylmethyl, isopropylcarbonylmethyl, n-butylcarbonylmethyl, tertbutylcarbonylmethyl, or where R4 and R5 together with the nitrogen atom or carbon atom to which they are respectively attached form a partially saturated ring having a total of 3 to 7 members which is
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PCT/EP2017/082832 optionally interrupted by one to three heteroatoms from the group consisting of N, O and S and optionally substituted further, if Q represents Q-13, Q-14 or Q-15,
R6 represents hydrogen, methyl, ethyl,
R8 represents hydrogen, halogen, cyano, nitro, hydrothio, hydroxy, methylamino, ethylamino, isopropylamino, n-propylamino, dimethylamino, diethylamino, cyclopropylamino, cyclobutylamino, cyclopentylamino, cyclohexylamino, methoxycarbonylmethylamino, methoxycarbonylethylamino, ethoxycarbonylmethylamino, ethoxycarbonylethylamino, methoxycarbonylamino, ethoxycarbonylamino, tert-butyloxycarbonylamino, phenylamino, Npiperidinyl, N-pyrrolidinyl, N-morpholinyl, methylaminocarbonylamino, ethylaminocarbonylamino, n-propylaminocarbonylamino, isopropylaminocarbonylamino, benzylaminocarbonylamino, phenylaminocarbonylamino, p-Clphenylaminocarbonylamino, mClphenylaminocarbonylamino, o-Clphenylaminocarbonylamino, cyclopropylaminocarbonylamino, cyclobutylaminocarbonylamino, cyclopentylaminocarbonylamino, cyclohexylaminocarbonylamino, dimethylaminocarbonylamino, methoxy, ethoxy, n-propyloxy, isopropyloxy, n-butyloxy, tertbutyloxy, methoxycarbonyloxy, ethoxycarbonyloxy, tert-butyloxycarbonyloxy, methylaminocarbonyloxy, ethylaminocarbonyloxy, n-propylaminocarbonyloxy, isopropylaminocarbonyloxy, benzylaminocarbonyloxy, phenylaminocarbonyloxy, cyclopropylaminocarbonyloxy, cyclobutylaminocarbonyloxy, cyclopentylaminocarbonyloxy, cyclohexylaminocarbonyloxy, dimethylaminocarbonyloxy, phenyloxy, p-Clphenyloxy, oClphenyloxy, m-Clphenyloxy, m-trifluorometiiylphenyloxy, p-trifluorometiiylphenyloxy, trifluorometiiyloxy, difluoromethyloxy, 2,2-difluoroethyloxy, 2,2,2-trifluoroetiiyloxy, methylthio, ethyltiiio, n-propyltitio, isopropyltitio, phenyltitio, p-Clphenyltitio, m-Clphenyltitio, o-Clphenylthio, pyridin-2-yltitio, pyridin-3-yltitio, benzyltitio, trifluorometiiyltitio, pentafluoroetiiyltitio, cyclopropyltitio, cyclobutyltitio, cyclopentyltitio, cyclohexyltitio, methylsulfinyl, ethylsulfinyl, n-propylsulfinyl, isopropylsulfinyl, n-butylsulfinyl, tertbutylsulfinyl, phenylsulfinyl, benzylsulfinyl, pyridin-2-ylsulfinyl, methylsulfonyl, ethylsulfonyl, n-propylsulfonyl, isopropylsulfonyl, n-butylsulfonyl, tert-butylsulfonyl, phenylsulfonyl, benzylsulfonyl, pyridin-2-ylsulfonyl, methyl, ethyl, n-propyl, 1-methylethyl, n-butyl, 1methylpropyl, 2-methylpropyl, 1,1-dimethylethyl, n-pentyl, 1-methylbutyl, 2-methylbutyl, 3methylbutyl, 1,1 -dimethylpropyl, 1,2-dimethylpropyl, 2,2-dimethylpropyl, 1 -ethylpropyl, nhexyl, 1-methylpentyl, 2-metiiylpentyl, 3-methylpentyl, 4-metiiylpentyl, 1,1-dimethylbutyl, 1,2dimethylbutyl, 1,3-dimethylbutyl, 2,2-dimetiiylbutyl, 2,3-dimethylbutyl, 3,3-dimethylbutyl, 1ethylbutyl, 2-etiiylbutyl, 1,1,2-trimethylpropyl, 1,2,2-trimethylpropyl, 1 -ethyl-1 -methylpropyl, 1 -etiiyl-2-metiiylpropyl, thiocyanate, isothiocyanate, formyl, ethenyl, 1 -propenyl, 2-propenyl, 1
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PCT/EP2017/082832 methyl-ethenyl, l-butenyl, 2-butenyl, 3-butenyl, 1-methyl-1-propenyl, 2-methyl-l-propenyl, 1methyl-2-propenyl, 2-methyl-2-propenyl, 1-pentenyl, 2-pentenyl, 3-pentenyl, 4-pentenyl, 1methyl-l-butenyl, 2-methyl-l-butenyl, 3-methyl-l-butenyl, 1-methyl-2-butenyl, 2-methyl-2butenyl, 3-methyl-2-butenyl, l-methyl-3-butenyl, 2-methyl-3-butenyl, 3-methyl-3-butenyl, 1,1dimethyl-2-propenyl, 1,2-dimethyl-1-propenyl, 1,2-dimethyl-2 -propenyl, 1-ethyl-1-propenyl, 1ethyl-2-propenyl, ethynyl, 1-propynyl, 2-propynyl, l-butynyl, 2-butynyl, 3-butynyl, l-methyl-2propynyl, 1-pentynyl, 2-pentynyl, 3-pentynyl, 4-pentynyl, 1-methyl-2-butynyl, l-methyl-3butynyl, 2-methyl-3-butynyl, 3-methyl-l-butynyl, 1,1-dimethyl-2-propynyl, 1-ethyl-2-propynyl, 1-hexynyl, 2-hexynyl, 3-hexynyl, 3,3-difluorocyclobut-l-yl, 3-fluorocyclobut-l-yl, 1fluorocyclobut-l-yl, 2,2-difluorocycloprop-l-yl, 1-fluorocycloprop-1-yl, 2-fluorocycloprop-l-yl, 4-fluorocyclohexyl, 4,4-difluorocyclohexyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, 1 methylcycloprop-1-yl, 2-methylcycloprop-1-yl, 2,2-dimethylcycloprop-l-yl, 2,3dimethylcyclopropyl, 1-cyanopropyl, 2-cyanopropyl, 1-methylcyclobutyl, 2-methylcyclobutyl,
3-methylcyclobutyl, 3,3-dimethylcyclobutyl, 1-cyanocyclobutyl, 2-cyanocyclobutyl, 3cyanocyclobutyl, 1 -allylcyclopropyl, 1 -vinylcyclobutyl, 1 -vinylcyclopropyl, 1 -ethylcyclopropyl, 1-methylcyclohexyl, 2-methylcyclohexyl, 3-methylcyclohexyl, 1-methoxycyclohexyl, 2methoxycyclohexyl, 3-methoxycyclohexyl, spiro[2.2]pent-l-yl, spiro[2.3]hex-l-yl, spiro[2.3]hex-4-yl, 3-spiro[2.3]hex-5-yl, spiro[3.3]hept-l-yl, spiro[3.3]hept-2-yl, bicyclo[ 1.1,0]butan-1 -yl, bicyclo[ 1.1,0]butan-2-yl, bicyclo[2.1,0]pentan-1 -yl, bicyclo[l. 1.1 ]pentan-l-yl, bicyclo[2.1,0]pentan-2-yl, bicyclo[2.1,0]pentan-5-yl, bicyclo[2.1.1]hexyl, bicyclo[2.2.1]hept-2-yl, bicyclo[2.2.2]octan-2-yl, bicyclo[3.2.1]octan-2-yl, bicyclo[3.2.2]nonan-2-yl, adamantan-l-yl, adamantan-2-yl, cyclopropylmethyl, cyclobutylmethyl, cyclopentylmethyl, cyclohexylmethyl, trifluoromethyl, pentafluoroethyl, 1,1,2,2-tetrafluoroethyl, heptafluoro-n-propyl, heptafluoroisopropyl, nonafluorobutyl, chlorodifluoromethyl, bromodifluoromethyl, dichlorofluoromethyl, iododifluoromethyl, bromo fluoromethyl, 1 -fluoroethyl, 2-fluoroethyl, fluoromethyl, difluoromethyl, 2,2difluoroethyl, 2,2,2-trifluoroethyl, difluoro-tert-butyl, chloromethyl, bromomethyl, fluoromethyl, 3,3,3-trifluoro-n-propyl, methoxycarbonyl, ethoxycarbonyl, isopropyloxycarbonyl, n-propyloxycarbonyl, n-butyloxycarbonyl, tert-butyloxycarbonyl, benzyloxycarbonyl, allyloxycarbonyl, methylaminocarbonyl, ethylaminocarbonyl, npropylaminocarbonyl, isopropylaminocarbonyl, benzylaminocarbonyl, phenylaminocarbonyl, cyclopropylaminocarbonyl, cyclobutylaminocarbonyl, cyclopentylaminocarbonyl, cyclohexylaminocarbonyl, dimethylaminocarbonyl, diethylaminocarbonyl, allylaminocarbonyl, pentafluorothio, methoxydifluoromethyl, ethoxydifluoromethyl, n-propyloxydifluoromethyl, trifluoromethoxymethyl, trifluoromethoxyethyl, trifluoromethoxy-n-propyl, methoxymethyl, ethoxymethyl, n-propyloxymethyl, ethoxyethyl, methoxyethyl, n-propyloxyethyl, methoxy-npropyl, ethoxy-n-propyl, 1 -methoxyeth-1 -yl, 1-methoxyprop-1-yl, l-ethoxyeth-l-yl, 2WO 2018/114596
PCT/EP2017/082832 methoxyprop-2-yl, 2-ethoxyprop-2-yl, methylthiomethyl, methylthioethyl, methylthio-n-propyl, ethylthiomethyl, trifluoromethylthiomethyl, pentafluoroethylthiomethyl, trifluoromethylthioethyl, trifluoromethylthio-n-propyl, methylcarbonyl, ethylcarbonyl, isopropylcarbonyl, n-butylcarbonyl, tert-butylcarbonyl, phenylcarbonyl, o-Clphenylcarbonyl, mClphenylcarbonyl, p-Clphenylcarbonyl, methoxycarbonylmethyl, ethoxycarbonylmethyl, methoxycarbonylethyl, ethoxycarbonylethyl, n-propyloxycarbonylmethyl, tertbutyloxycarbonylmethyl, tert-butyloxycarbonylethyl, hydroxycarbonylmethyl, hydroxycarbonylethyl, hydroxycarbonyl, methylaminocarbonylmethyl, ethylaminocarbonylmethyl, n-propylaminocarbonylmethyl, isopropylaminocarbonylmethyl, benzylaminocarbonylmethyl, phenylaminocarbonylmethyl, cyclopropylaminocarbonylmethyl, cyclobutylaminocarbonylmethyl, cyclopentylaminocarbonylmethyl, cyclohexylaminocarbonylmethyl, dimethylaminocarbonylmethyl, diethylaminocarbonylmethyl, allylaminocarbonylmethyl, methylaminomethyl, dimethylaminomethyl, diethylaminomethyl, ethylaminomethyl, isopropylaminomethyl, n-propylaminomethyl, n-butylaminomethyl, methylaminoethyl, dimethylaminoethyl, diethylaminoethyl, N-pyrrolidinylmethyl, Npiperidinylmethyl, hydroxyimino, methoxyimino, ethoxyimino, n-propyloxyimino, nbutyloxyimino, isopropyloxyimino, tert-butyloxyimino, cyclopropylmethoxyimino, cyclobutylmethoxyimino, cyclopentylmethoxyimino, cyclohexylmethoxyimino, benzyloxyimino, phenyloxyimino, allyloxyimino, p-Clphenylmethyloxyimino, phenylethynyl, p-Clphenylethynyl, m-Clphenylethynyl, o-Clphenylethynyl, p-F-phenylethynyl, m-Fphenylethynyl, o-F-phenylethynyl, pyridin-2-ylethynyl, pyridin-3-ylethynyl, thiophen-2ylethynyl, trimethylsilylethynyl, triethylsilylethynyl, tri(isopropyl)silylethynyl, cyclopropylethynyl, cyclobutylethynyl, cyclopentylethynyl, cyclohexylethynyl, phenyl, benzyl, p-Clphenyl, m-Clphenyl, o-Clphenyl, p-F-phenyl, m-F-phenyl, o-F-phenyl, ptrifluoromethylphenyl, m-trifluoromethylphenyl, o-trifluoromethylphenyl, p-methylphenyl, mmethylphenyl, o-methylphenyl, p-methoxyphenyl, m-methoxyphenyl, o-methoxyphenyl, pClphenylmethyl, m-Clphenylmethyl, o-Clphenylmethyl, pyridin-2-yl, pyridin-3-yl, pyridin-4-yl, thiophen-2-yl, thiophen-3-yl, furan-2-yl, furan-3-yl, pyrimidin-2-yl, pyrazin-2-yl, methoxymethoxymethyl, ethoxyethoxymethyl, methoxyethoxymethyl, methylaminosulfonylamino, dimethylaminosulfonylamino, ethylaminosulfonylamino, diethylaminosulfonylamino, isopropylaminosulfonylamino, cyclopropylaminosulfonylamino, cyclobutylaminosulfonylamino, cyclopentylaminosulfonylamino, cyclohexylaminosulfonylamino, diazo, phenyldiazo, trimethylsilyl, tri(isopropyl)silyl, triethylsilyl, dimethyl(phenyl)silyl, diphenyl(methyl)silyl, or where A1 and A2, when each is a group C-R8, together with the atoms to which they are attached form a partially saturated or fully unsaturated 5- to 7-membered ring which is
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PCT/EP2017/082832 optionally interrupted by heteroatoms from the group consisting of N, O and S and optionally substituted further, or where A2 and A3, when each is a group C-R8, together with the atoms to which they are attached form a partially saturated or fully unsaturated 5- to 7-membered ring which is optionally interrupted by heteroatoms from the group consisting of N, O and S and optionally substituted further, or where A3 and A4, when each is a group C-R8, together with the atoms to which they are attached form a partially saturated or fully unsaturated 5- to 7-membered ring which is optionally interrupted by heteroatoms from the group consisting of N, O and S and optionally substituted further and
W represents oxygen.
The invention especially provides compounds of the general formula (I) in which
X and Y independently of one another represent C-H or the moiety C-R1, where
X represents C-H if Y represents the moiety C-R1 and
X represents the moiety C-R1 if Y represents C-H,
R1 represents chlorine, bromine, iodine, methyl, ethyl, n-propyl, 1 -methylethyl, n-butyl, 1 methylpropyl, 2-methylpropyl, 1,1-dimethylethyl, n-pentyl, 1-methylbutyl, 2-metiiylbutyl, 3methylbutyl, 1,1 -dimethylpropyl, 1,2-dimethylpropyl, 2,2-dimethylpropyl, 1 -ethylpropyl, nhexyl, 1-methylpentyl, 2-metiiylpentyl, 3-methylpentyl, 4-metiiylpentyl, 1,1-dimethylbutyl, 1,2dimethylbutyl, 1,3-dimethylbutyl, 2,2-dimetiiylbutyl, 2,3-dimethylbutyl, 3,3-dimethylbutyl, 1ethylbutyl, 2-etiiylbutyl, 1,1,2-trimethylpropyl, 1,2,2-trimethylpropyl, 1 -ethyl-1 -methylpropyl, 1 -etiiyl-2-metiiylpropyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, adamantan-l-yl, adamantan-2-yl, 1-methylcyclopropyl, 2-methylcyclopropyl, 2,2-dimethylcyclopropyl, 2,3dimethylcyclopropyl, l,l'-bi(cyclopropyl)-l-yl, l,l'-bi(cyclopropyl)-2-yl, 2'-methyl-l,Tbi(cyclopropyl)-2-yl, 1 -cyanocyclopropyl, 2-cyanocyclopropyl, 1 -methylcyclobutyl, 2methylcyclobutyl, 3-methylcyclobutyl, 3,3-dimethylcyclobut-l-yl, 3,3-difluorocyclobut-l-yl, 3fluorocyclobut-1-yl, 2,2-difluorocycloprop-l-yl, 1-fluorocycloprop-1-yl, 2-fluorocycloprop-lyl, 1-ethylcyclopropyl, 1-methylcyclohexyl, 2-methylcyclohexyl, 3-methylcyclohexyl, 1methoxycyclohexyl, 2-methoxycyclohexyl, 3-methoxycyclohexyl, trifluoromethyl,
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PCT/EP2017/082832 pentafluoroethyl, 1,1,2,2-tetrafluoroethyl, heptafluoropropyl, nonafluorobutyl, chlorodifluoromethyl, difluoromethyl, 2,2-difluoroethyl, 2,2,2-trifluoroethyl, difluoro-tert-butyl, methoxy, ethoxy, n-propyloxy, isopropyloxy, n-butyloxy, tert-butyloxy, methoxymethyl, ethoxymethyl, methoxyethyl, ethoxyethyl, trifluoromethoxy, difluoromethoxy, 2,2,2trifluoroethoxy, 2,2-difluoroethoxy, methylthio, ethylthio, trifluoromethylthio, pentafluoroethylthio, phenyl, phenyloxy, p-Clphenyloxy, thiophen-2-yl, thiophen-3-yl, pyridin2-yl, pyridin-3-yl, pyridin-4-yl, furan-2-yl, furan-3-yl, cyclopropylmethyl, cyclobutylmethyl, cyclopentylmethyl, cyclohexylmethyl, ethenyl, 1 -propenyl, 2-propenyl, 1 -methylethenyl, 1 butenyl, 2-butenyl, 3-butenyl, 1-methyl-1-propenyl, 2-methyl-1-propenyl, 1-methyl-2-propenyl, 2-methyl-2-propenyl, 1-pentenyl, 2-pentenyl, 3-pentenyl, 4-pentenyl, prop-2-en-l-yloxy, but-3en-l-yloxy, pent-4-en-1-yloxy, ethynyl, 1-propynyl, 2-propynyl, l-butynyl, 1-pentynyl, 1hexynyl, 2-(trimethylsilyl)ethyn-1 -yl, 2-(triethylsilyl)ethyn-1 -yl, 2-(triisopropylsilyl)ethyn-1 -yl, amino, methylamino, ethylamino, dimethylamino, diethylamino,
R3 represents hydroxy, methoxy, ethoxy, n-propyloxy, 1 -methylethoxy, n-butyloxy, 1 methylpropyloxy, 2-methylpropyloxy, 1,1 -dimethylethoxy, n-pentyloxy, cyclopropylmethoxy, cyclobutylmethoxy, cyclopentylmethoxy, cyclohexylmethoxy, benzyloxy, pchlorophenylmethoxy, m-chlorophenylmethoxy, o-chlorophenylmethoxy, pmethoxyphenylmethoxy, methoxymethoxy, methoxyethoxy, methoxy-n-propyloxy, ethoxymethoxy, ethoxyethoxy, methylcarbonyloxy, ethylcarbonyloxy, n-propylcarbonyloxy, 1methylefliylcarbonyloxy, n-butylcarbonyloxy, 1 -methylpropylcarbonyloxy, 2methylpropylcarbonyloxy, 1,1 -dimethylethylcarbonyloxy, n-pentylcarbonyloxy, phenylcarbonyloxy, p-chlorophenylcarbonyloxy, m-chlorophenylcarbonyloxy, ochlorophenylcarbonyloxy, p-fluorophenylcarbonyloxy, m-fluorophenylcarbonyloxy, ofluorophenylcarbonyloxy, cyclopropylcarbonyloxy, cyclobutylcarbonyloxy, cyclopentylcarbonyloxy, cyclohexylcarbonyloxy, trifluoromethylcarbonyloxy, difluoromethylcarbonyloxy, methoxycarbonyloxy, ethoxycarbonyloxy, npropyloxycarbonyloxy, isopropyloxycarbonyloxy, n-butyloxycarbonyloxy, 1,1dimethylethyloxycarbonyloxy, 2,2-dimethylpropyloxycarbonyloxy, pyridin-2-ylcarbonyloxy, pyridin-3-ylcarbonyloxy, pyridin-4-ylcarbonyloxy, 4-trifluoromethylpyridin-3-ylcarbonyloxy, allylcarbonyloxy, methylsulfonyloxy, ethylsulfonyloxy, n-propylsulfonyloxy, 1 methylethylsulfonyloxy, cyclopropylsulfonyloxy,
R6 represents hydrogen,
W represents oxygen
WO 2018/114596
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Q represents one of the moieties Q-l.l to Q-29.5 specifically mentioned in the table below:
_N tr .N. 5-Γ .N. ~ tv /—s .N. V .N.
Q-l.l Q-1.2 Q-1.3 Q-1.4 Q-1.5
.N. tv y—s .N. V .N. — .N. — V LL
Q-1.6 Q-1.7 Q-1.8 Q-1.9 Q-1.10
XN. -N .N .N. Γ .N. >v —s
Q-l.l 1 Q-1.12 Q-1.13 Q-1.14 Q-1.15
.N. ir O—X / .N. .N. ~ V .N. ~ yr <pci _N yr rs
Q-1.16 Q-1.17 Q-1.18 Q-1.19 Q-1.20
.N. w \=N .N. W / .N. s —_^=N .N. W .N. W
Q-2.1 Q-2.2 Q-2.3 Q-2.4 Q-2.5
.N. s ^=N .N. svV .N. ~ r .N. ~ <Y .N. r
Q-2.6 Q-2.7 Q-2.8 Q-2.9 Q-2.10
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d~ AL ~ S y t? -N χΝ. y
Q-2.11 Q-2.12 Q-2.13 Q-2.14 Q-2.15
_N ~ s J=N /N=\ Vs -N S H —s _N. — s y^ <r »y- £ -N \y~ Cl
Q-2.16 Q-2.17 Q-2.18 Q-2.19 Q-2.20
χΝ. χΝ. jjr yr
Q-3.1 Q-3.2 Q-3.3 Q-3.4 Q-3.5
-N s' χΝ. y .N. ~ .N. ~ y _N.
Q-3.6 Q-3.7 Q-3.8 Q-3.9 Q-3.10
AL / AL A / y AL s'
Q-3.11 Q-3.12 Q-3.13 Q-3.14 Q-3.15
AL s' yo -N —s AL s' <vj Cl f p cr
Q-3.16 Q-3.17 Q-3.18 Q-3.19 Q-3.20
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-Ν Z .N. s' Ο \ s' F-Z F F F
Q-3.21 Q-3.22 Q-3.23 Q-3.24 Q-3.25
Figure AU2017379281A1_D0010
'Cr Z
Q-4.1 Q-4.2 Q-4.3 Q-4.4 Q-4.5
Λ__, z z z z
Q-4.6 Q-4.7 Q-4.8 Q-4.9 Q-4.10
z z z z
Q-4.11 Q-4.12 Q-4.13 Q-4.14 Q-4.15
Figure AU2017379281A1_D0011
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-N. ΌΓ .Ν. -Ν. -Ν.
Q-5.1 Q-5.2 Q-5.3 Q-5.4 Q-5.5
Αχ Αχ- -Ν.
Q-5.6 Q-5.7 Q-5.8 Q-5.9 Q-5.10
Αχ- Ay- V dr
Q-5.ll Q-5.12 Q-5.13 Q-5.14 Q-5.15
Ο-γχ- ίΑχ- Αχ F F
Q-5.16 Q-5.17 Q-5.18 Q-5.19 Q-5.20
-Ν νΓ χΝ. >Γ ,Ν. VY^ / 0 ,Ν. _Ν.
Q-6.1 Q-6.2 Q-6.3 Q-6.4 Q-6.5
χΝ. / ° _Ν. Ar ΧΝ. ΧΝ. Rr
Q-6.6 Q-6.7 Q-6.8 Q-6.9 Q-6.10
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-N -N — -N. y
Q-6.11 Q-6.12 Q-6.13 Q-6.14 Q-6.15
-N. -- tv / 0 O-~f / ZNV -N. ~ r -N. ~ yr <pci ZNV r
Q-6.16 Q-6.17 Q-6.18 Q-6.19 Q-6.20
<r o -N. -- ir 0 Cl ZN. -- V V/ Cr o '—N -N. yr 0-c,
Q-6.21 Q-6.22 Q-6.23 Q-6.24 Q-6.25
Al. °vV \=N -N. Γ -N. — o —_^=N -N. — tv <v
Q-7.1 Q-7.2 Q-7.3 Q-7.4 Q-7.5
-N. o —/~~^=N -N. — tv ZNV ~ o' zr ZNV o' tr ZNK o' r
Q-7.6 Q-7.7 Q-7.8 Q-7.9 Q-7.10
ZN. tv r -N. o' r -N. tv t? -N. — tv ZNK -- o r
Q-7.11 Q-7.12 Q-7.13 Q-7.14 Q-7.15
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o' V-* o' ,^r -N — <s ZNK XN. ~ Cl
Q-7.16 Q-7.17 Q-7.18 Q-7.19 Q-7.20
χΝ. ,N. ,N.
Q-8.1 Q-8.2 Q-8.3 Q-8.4 Q-8.5
χΝ. o' ,N. ¥ ZNV ~ <r _N. Z
Q-8.6 Q-8.7 Q-8.8 Q-8.9 Q-8.10
Figure AU2017379281A1_D0012
Figure AU2017379281A1_D0013
Figure AU2017379281A1_D0014
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Figure AU2017379281A1_D0015
Figure AU2017379281A1_D0016
χΝ. — χΝ. -T NC \ -N. ~ —o -N. /~°
Q-8.36 Q-8.37 Q-8.38 Q-8.39 Q-8.40
Figure AU2017379281A1_D0017
Figure AU2017379281A1_D0018
Figure AU2017379281A1_D0019
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Figure AU2017379281A1_D0020
Figure AU2017379281A1_D0021
Figure AU2017379281A1_D0022
Figure AU2017379281A1_D0023
-N. tr -N
Q-9.1 Q-9.2 Q-9.3 Q-9.4 Q-9.5
-N. .N. Ar -N. £
Q-9.6 Q-9.7 Q-9.8 Q-9.9 Q-9.10
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.n. ~ GT .N. G-r Cl .N. G-r
Q-9.11 Q-9.12 Q-9.13 Q-9.14 Q-9.15
Ar .N. ir Ny- .N. Άγ
Q-9.16 Q-9.17 Q-9.18 Q-9.19 Q-9.20
.N. vr .N .N vr _N.
Q-10.1 Q-10.2 Q-10.3 Q-10.4 Q-10.5
He Hx _N. r
Q-10.6 Q-10.7 Q-10.8 Q-10.9 Q-10.10
Ar Hr V r
Q-10.11 Q-10.12 Q-10.13 Q-10.14 Q-10.15
V y—o Q Ay a w Ay F
Q-10.16 Q-10.17 Q-10.18 Q-10.19 Q-10.20
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Λν / N
Q-ll.l Q-11.2 Q-11.3 Q-11.4 Q-11.5
<z T £ •Λ z d)^ d'
Q-11.6 Q-11.7 Q-11.8 Q-11.9 Q-11.10
d'r' r 'A: LL d'r' /“N 0—f / •Crr d Cl
Q-ll.ll Q-11.12 Q-11.13 Q-11.14 Q-11.15
dr' γτ-
Q-12.1 Q-12.2 Q-12.3 Q-12.4 Q-12.5
z Z z z z
Q-12.6 Q-12.7 Q-12.8 Q-12.9 Q-12.10
z LL z z z z
Q-12.11 Q-12.12 Q-12.13 Q-12.14 Q-12.15
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ir ~A Cl —-/ Br
Q-12.16 Q-12.17 Q-12.18 Q-12.19 Q-12.20
Figure AU2017379281A1_D0024
z F r
Q-12.26 Q-12.27 Q-12.28 Q-12.29 Q-12.30
^-NZ P^ ^n y- ^-n y-*’ ^n y-
Q-13.1 Q-13.2 Q-13.3 Q-13.4 Q-13.5
^-NZ PT ^-NZ hT T F
Q-13.6 Q-13.7 Q-13.8 Q-13.9 Q-13.10
f0 \ ZNK — /t-nz y* Azy^
Q-13.11 Q-13.12 Q-13.13 Q-13.14 Q-13.15
Fy Azy^
Q-13.16 Q-13.17 Q-13.18 Q-13.19 Q-13.20
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χΝ. — hnx y-* χΝ hn Ύ* ^-N ·γ-* -N. hnz F Π Q /
Q-13.21 Q-13.22 Q-13.23 Q-13.24 Q-13.25
Figure AU2017379281A1_D0025
Figure AU2017379281A1_D0026
_N. HN' τΛ _ χΝ. _ ^n -y-*’ Cl~Ά ,N HN _ XNK '-ν' y--' -N HN 'V''^
Q-13.36 Q-13.37 Q-13.38 Q-13.39 Q-13.40
/rtr Ovy^ xNK ν' %-·’
Q-13.36 Q-13.37 Q-13.38 Q-13.39 Q-13.40
-N. hn' XN. hn' ·γ-^ -N. hn' y-* -N. hn' y-* χΝ. hn' Ύ* F
Q-13.41 Q-13.42 Q-13.43 Q-13.44 Q-13.45
,N HN' V^ —s _ XNV n y- F _ XN. _ N\ FFf χΝ. HN\ FFf
Q-13.46 Q-13.47 Q-13.48 Q-13.49 Q-13.50
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^-n y- nc~a ^-n y-*’ y-*
Q-13.51 Q-13.52 Q-13.53 Q-13.54 Q-13.55
Figure AU2017379281A1_D0027
^n y-*’ F F qir XN. -. ςτ ccr
Q-13.61 Q-13.62 Q-13.63 Q-13.64 Q-13.65
^n y-*’ o J^° %O —o CK-/y- HO n.
Q-13.66 Q-13.67 Q-13.68 Q-13.69 Q-13.70
Figure AU2017379281A1_D0028
Figure AU2017379281A1_D0029
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.N. tr \ .N. tr .N. tr Λ Cr .N. tr
Q-14.1 Q-14.2 Q-14.3 Q-14.4 Q-14.5
.N. ΛΤ \ .N. tr «—N \ «—N \
Q-14.6 Q-14.7 Q-14.8 Q-14.9 Q-14.10
.N. /N. .N. r Air \ .N. jr
Q-14.11 Q-14.12 Q-14.13 Q-14.14 Q-14.15
.N. tr H .N. r «—N H .N. tr Λ H H
Q-14.16 Q-14.17 Q-14.18 Q-14.19 Q-14.20
_n. — H Ύτ H N—J H Hr H Hr H
Q-15.1 Q-15.2 Q-15.3 Q-15.4 Q-15.5
-N. <r / Ύτ / N—J / Hr / Hr /
Q-15.6 Q-15.7 Q-15.8 Q-15.9 Q-15.10
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Jjr 0r -N. -N Or λ -N. CK -i
Q-15.11 Q-15.12 Q-15.13 Q-15.14 Q-15.15
/ Ύτ Λ ~Cr t/r
Q-15.16 Q-15.17 Q-15.18 Q-15.19 Q-15.20
/ Ύτ 0 Oyr N—J / -N. .n. -
Q-15.21 Q-15.22 Q-15.23 Q-15.24 Q-15.25
-N. 0 Cl Tr· 0 Cl 'sYr / .N.
Q-15.26 Q-15.27 Q-15.28 Q-15.29 Q-15.30
Cr u cr cr N cr
Q-16.1 Q-16.2 Q-16.3 Q-16.4 Q-16.5
CT Cl ςτ Qr Cl LL Cr
Q-16.6 Q-16.7 Q-16.8 Q-16.9 Q-16.10
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ΐ o / FtF
Q-16.11 Q-16.12 Q-16.13 Q-16.14 Q-16.15
Figure AU2017379281A1_D0030
^N. - .XX Qr Cl ?
Q-16.21 Q-16.22 Q-16.23 Q-16.24 Q-16.25
A^r fTf Ά A A
Q-16.26 Q-16.27 Q-16.28 Q-16.29 Q-16.30
AA A N—ά H Λ
Q-16.31 Q-16.32 Q-16.33 Q-16.34 Q-16.35
XX F F N—Z Cl H -π -Π
Q-16.36 Q-16.37 Q-16.38 Q-16.39 Q-16.40
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r X LL ό-Α '—o \
Q-16.41 Q-16.42 Q-16.43 Q-16.44 Q-16.45
XV Xr Π χτ Cl XT F Cl
Q-16.46 Q-16.47 Q-16.48 Q-16.49 Q-16.50
XT Xr N ίχ CI^^N
Q-16.51 Q-16.52 Q-16.53 Q-16.54 Q-16.55
Figure AU2017379281A1_D0031
Figure AU2017379281A1_D0032
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Cl N*Ny- CI^^A N>NXr-*’ X Cl N>NXr-*’ 7’
Q-16.66 Q-16.67 Q-16.68 Q-16.69 Q-16.70
ψθτ Xr Cl h F Xr F rF
Q-16.71 Q-16.72 Q-16.73 Q-16.74 Q-16.75
AT Qr Cl r^r AJ Xr
Q-16.76 Q-16.77 Q-16.78 Q-16.79 Q-16.80
Cr Xr Mr- N—J N—J
Q-17.1 Q-17.2 Q-17.3 Q-17.4 Q-17.5
N—J A Mr- N—J M/^ N—J
Q-17.6 Q-17.7 Q-17.8 Q-17.9 Q-17.10
Xr Χχ X°_r~ N—J Χχτ N—J
Q-18.1 Q-18.2 Q-18.3 Q-18.4 Q-18.5
'XCjT' N—J A XjT N—J N—J
Q-18.6 Q-18.7 Q-18.8 Q-18.9 Q-18.10
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Cr' N—N H YY N—N \ YY N— YY N—N V YY N—N X
Q-19.1 Q-19.2 Q-19.3 Q-19.4 Q-19.5
VY N—N \ Avy N—N H Yy N—N \ Zr N—N \ r N—N \
Q-19.6 Q-19.7 Q-19.8 Q-19.9 Q-19.10
Ay N—N b \ N—N \ Avy N—N \ Yy N—N b
Q-19.11 Q-19.12 Q-19.13 Q-19.14 Q-19.15
.N. o' K .N. z .N. Y .N. Y .N. Cl
Q-20.1 Q-20.2 Q-20.3 Q-20.4 Q-20.5
r—O C Y O-N Yy O'N <Y <Y Γ <Y /—N
Q-21.1 Q-22.2 Q-23.1 Q-23.2 Q-23.3
<Y r £y ZN <Y ZN <Y x CY y”n
Q-23.4 Q-23.5 Q-23.6 Q-23.7 Q-23.8
<Y z <Y z <Y Y <Y V <Y Y
Q-23.9 Q-23.10 Q-23.11 Q-23.12 Q-23.13
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z~N —o z~N —s X Cl F
Q-23.14 Q-23.15 Q-23.16 Q-23.17 Q-23.18
\ Z“N o /-N L vv “· 1 0^ O--. X O—.
Q-23.19 Q-23.20 Q-23.21 Q-23.22 Q-23.23
Γ 0^ t>0- 0^ X °Λ
Q-23.24 Q-23.25 Q-23.26 Q-23.27 Q-23.28
z-N z-N Cr Cr Cr
s s s \ s \ s \
04 04 < o—
F F F F F F F F
Q-23.29 Q-23.30 Q-23.31 Q-23.32 Q-23.33
z-N o ? o— VkA* LL F F Vs 0^ --Vs
Q-23.34 Q-23.35 Q-23.36 Q-23.37 Q-23.38
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-Or r -Or r< d d o \ F F
Q-23.39 Q-23.40 Q-23.41 Q-23.42 Q-23.43
-Or d' d Cl o o d' o—
Q-23.44 Q-23.45 Q-23.46 Q-23.47 Q-23.48
dd 7 A o /
Q-23.49 Q-23.50 Q-23.51 Q-23.52 Q-23.53
NH / O<N NH Λ °^N NH d O<N NH °^N o (
Q-23.54 Q-23.55 Q-23.56 Q-23.57 Q-23.58
.N. N—N H -N. N—N / .N. f y^ ^N—N Vy^ N—N / -N. /r N—N A
Q-25.1 Q-25.2 Q-25.3 Q-25.4 Q-25.5
'Xr' N—N / N-N / N-N / .N. _ f y^ N—N ry _N. N—N
Q-25.6 Q-25.7 Q-25.8 Q-25.9 Q-25.10
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N—N o—-/ / f y~ Ji—n -N. — f y^ N—N r-7 —o -N. f y^ yy-N _N. (Ό N—N <f
Q-25.11 Q-25.12 Q-25.13 Q-25.14 Q-25.15
N—N / N—N / s-^Ny-*· __^N—N N—N N—N 7(
Q-25.16 Q-25.17 Q-25.18 Q-25.19 Q-25.20
X N—N 0 X N—N 0 f3c X N—N 0 Cl X N—N 0 cf3 X O' N—N 0 Cl
Q-25.21 Q-25.22 Q-25.23 Q-25.24 Q-25.25
N—N 0 N—N 0 f3c N—N 0 Cl N—N 0 cf3 N—N 0 Cl
Q-25.26 Q-25.27 Q-25.28 Q-25.29 Q-25.30
F3c-^>Ny^ N—N 0 F.cy^ N—N 0 f3c F-cW N—N 0 Cl N—N 0 cf3 F,cYy^ N—N 0 Cl
Q-25.31 Q-25.32 Q-25.33 Q-25.34 Q-25.35
N—N 0 XfNy^ N—N 0 f3c N—N 0 Cl N—N 0 cf3 XfNy^ N-N 0 Cl
Q-25.36 Q-25.37 Q-25.38 Q-25.39 Q-25.40
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Figure AU2017379281A1_D0033
.N. iY^ N—N \ .N. <y^ N—N ) .N. N—N r N—N \ Z'v N—N \
Q-26.1 Q-26.2 Q-26.3 Q-26.4 Q-26.5
Ay N-N \ .N. <y^ N—N r- XN. ~ <Τ~ N-N V Sb N-N \ N—N \
Q-26.6 Q-26.7 Q-26.8 Q-26.9 Q-26.10
Sv N—N H _N. <y^ N—N b .N. iY^ N—N b ΖίΆ N—N \ O-w N—N \
Q-26.11 Q-26.12 Q-26.13 Q-26.14 Q-26.15
.N. er N—N \ .N. N—N ) .N. /Y N—N b .N. /Y N—N b XN. % Y^ N—N^
Q-27.1 Q-27.2 Q-27.3 Q-27.4 Q-27.5
N\ n N—N / N\ n _ ^N—N N\ it N—N b N\ it v N—N b N\ IT N—N
Q-28.1 Q-28.2 Q-28.3 Q-28.4 Q-28.5
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n\ N—J / N\ J ^N—J N\ J N—' Λ N\ J \ N—J λ /Λ
Q-29.1 Q-29.2 Q-29.3 Q-29.4 Q-29.5
The invention particularly especially provides compounds of the general formula (I) in which
X and Y independently of one another represent C-H or the moiety C-R1, where
X represents C-H if Y represents the moiety C-R1 and
X represents the moiety C-R1 if Y represents C-H,
R1 represents methyl, ethyl, n-propyl, 1 -methylethyl, n-butyl, 1 -methylpropyl, 2-methylpropyl, 1,1dimethyletiiyl, n-pentyl, 1-methylbutyl, 2-methylbutyl, 3-methylbutyl, 1,1-dimethylpropyl, 1,2dimethylpropyl, 2,2-dimethylpropyl, 1-ethylpropyl, n-hexyl, 1-methylpentyl, 2-methylpentyl, 3methylpentyl, 4-methylpentyl, 1,1-dimethylbutyl, 1,2-dimethylbutyl, 1,3-dimethylbutyl, 2,2dimethylbutyl, 2,3-dimethylbutyl, 3,3-dimethylbutyl, 1-ethylbutyl, 2-ethylbutyl, 1,1,2trimethylpropyl, 1,2,2-trimetiiylpropyl, 1-ethyl-1-methylpropyl, 1-ethyl-2-methylpropyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, adamantan-l-yl, adamantan-2-yl, 1methylcyclopropyl, 2-methylcyclopropyl, 2,2-dimethylcyclopropyl, 2,3-dimethylcyclopropyl, l,l'-bi(cyclopropyl)-l-yl, l,l'-bi(cyclopropyl)-2-yl, 2'-methyl-l,T-bi(cyclopropyl)-2-yl, 1cyanocyclopropyl, 2-cyanocyclopropyl, 1-methylcyclobutyl, 2-methylcyclobutyl, 3methylcyclobutyl, 3,3-dimethylcyclobut-l-yl, 3,3-difluorocyclobut-l-yl, 3-fluorocyclobut-l-yl,
2,2-difluorocycloprop-1 -yl, 1-fluorocycloprop-1-yl, 2-fluorocycloprop-1 -yl, 1-ethylcyclopropyl,
1- methylcyclohexyl, 2-methylcyclohexyl, 3-methylcyclohexyl, 1-methoxycyclohexyl, 2methoxycyclohexyl, 3-methoxycyclohexyl, trifluoromethyl, pentafluoroethyl, 1,1,2,2tetrafluoroethyl, heptafluoropropyl, nonafluorobutyl, chlorodifluoromethyl, difluoromethyl, 2,2difluoroethyl, 2,2,2-trifluoroethyl, difluoro-tert-butyl, methoxy, ethoxy, n-propyloxy, isopropyloxy, n-butyloxy, tert-butyloxy, methoxymethyl, ethoxymethyl, methoxyethyl, ethoxyethyl, trifluoromethoxy, difluoromethoxy, 2,2,2-trifluoroethoxy, 2,2-difluoroethoxy, methylthio, ethyltiiio, trifluorometiiyltitio, pentafluoroethyltiiio, phenyl, phenyloxy, pClphenyloxy, titiophen-2-yl, titiophen-3-yl, pyridin-2-yl, pyridin-3-yl, pyridin-4-yl, furan-2-yl, furan-3-yl, cyclopropylmethyl, cyclobutylmethyl, cyclopentylmethyl, cyclohexylmethyl, ethenyl, 1-propenyl, 2-propenyl, 1-methylethenyl, l-butenyl, 2-butenyl, 3-butenyl, 1-methyl-1propenyl, 2-methyl-1-propenyl, 1 -metiiyl-2-propenyl, 2-methyl-2-propenyl, 1-pentenyl, 2pentenyl, 3-pentenyl, 4-pentenyl, prop-2-en-l-yloxy, but-3-en-l-yloxy, pent-4-en-l-yloxy, ethynyl, 1-propynyl, 2-propynyl, l-butynyl, 1-pentynyl, 1-hexynyl, 2-(trimethylsilyl)etiiyn-l-yl,
2- (triethylsilyl)ethyn-1 -yl, 2-(triisopropylsilyl)ethyn-1 -yl,
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R3 represents hydroxy, methoxy, ethoxy, n-propyloxy, 1 -methylethoxy, n-butyloxy, 1 methylpropyloxy, 2-methylpropyloxy, 1,1 -dimethylethoxy, n-pentyloxy, cyclopropylmethoxy, cyclobutylmethoxy, cyclopentylmethoxy, cyclohexylmethoxy, benzyloxy, pchlorophenylmethoxy, m-chlorophenylmethoxy, o-chlorophenylmethoxy, pmethoxyphenylmethoxy, methoxymethoxy, methoxyethoxy, methoxy-n-propyloxy, ethoxymethoxy, ethoxyethoxy, methylcarbonyloxy, ethylcarbonyloxy, n-propylcarbonyloxy, 1methylethylcarbonyloxy, n-butylcarbonyloxy, 1 -methylpropylcarbonyloxy, 2methylpropylcarbonyloxy, 1,1 -dimethylethylcarbonyloxy, n-pentylcarbonyloxy, phenylcarbonyloxy, p-chlorophenylcarbonyloxy, m-chlorophenylcarbonyloxy, ochlorophenylcarbonyloxy, p-fluorophenylcarbonyloxy, m-fluorophenylcarbonyloxy, ofluorophenylcarbonyloxy, cyclopropylcarbonyloxy, cyclobutylcarbonyloxy, cyclopentylcarbonyloxy, cyclohexylcarbonyloxy, trifluoromethylcarbonyloxy, difluoromethylcarbonyloxy, methoxycarbonyloxy, ethoxycarbonyloxy, npropyloxycarbonyloxy, isopropyloxycarbonyloxy, n-butyloxycarbonyloxy, 1,1dimethylethyloxycarbonyloxy, 2,2-dimethylpropyloxycarbonyloxy, pyridin-2-ylcarbonyloxy, pyridin-3-ylcarbonyloxy, pyridin-4-ylcarbonyloxy, 4-trifluoromethylpyridin-3-ylcarbonyloxy, allylcarbonyloxy, methylsulfonyloxy, ethylsulfonyloxy, n-propylsulfonyloxy, 1 methylethylsulfonyloxy, cyclopropylsulfonyloxy,
R6 represents hydrogen,
W represents oxygen and
Q represents one of the moieties Q-l.l to Q-29.5 specifically mentioned in the table below, particularly preferably with the exception of the radicals Q-8.7, Q-13.5 and Q-16.61 listed in the table above if X represents C-methyl or C-methoxy and in both cases Y simultaneously represents C-H.
The definitions of radicals listed above in general terms or within areas of preference apply both to the end products of the formula (1) and correspondingly to the starting materials or intermediates required for preparation in each case. These radical definitions can be combined with one another as desired, i.e. including combinations between the given preferred ranges.
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Primarily for reasons of higher herbicidal activity, better selectivity and/or better producibility, compounds of the abovementioned formula (I) according to the invention or their salts or their use according to the invention are of particular interest in which individual radicals have one of the preferred meanings already specified or specified below, or in particular those in which one or more of the preferred meanings already specified or specified below occur in combination.
With regard to the compounds according to the invention, the terms used above and further below will be elucidated. These are familiar to the person skilled in the art and especially have the definitions elucidated hereinafter:
Unless defined differently, names of chemical groups are generally to be understood such that attachment to the skeleton or the remainder of the molecule is via the structural element mentioned last, i.e. for example in the case of (C2-Cs)-alkenyloxy via the oxygen atom and in the case of heterocyclyl(Ci-Cs)-alkyl or R12O(O)C-(Ci-Cs)-alkyl in each case via the carbon atom of the alkyl group.
According to the invention, alkylsulfonyl - alone or as part of a chemical group - refers to straightchain or branched alkylsulfonyl, preferably having 1 to 8 or 1 to 6 carbon atoms, for example (but not limited to) (Ci-Cej-alkylsulfonyl such as methylsulfonyl, ethylsulfonyl, propylsulfonyl, 1methyletiiylsulfonyl, butylsulfonyl, 1 -methylpropylsulfonyl, 2-methylpropylsulfonyl, 1,1dimethylethylsulfonyl, pentylsulfonyl, 1-methylbutylsulfonyl, 2-methylbutylsulfonyl, 3methylbutylsulfonyl, 1,1 -dimethylpropylsulfonyl, 1,2-dimetiiylpropylsulfonyl, 2,2dimethylpropylsulfonyl, 1 -ethylpropylsulfonyl, hexylsulfonyl, 1 -methylpentylsulfonyl, 2methylpentylsulfonyl, 3-methylpentylsulfonyl, 4-metiiylpentylsulfonyl, 1,1-dimethylbutylsulfonyl, 1,2dimethylbutylsulfonyl, 1,3-dimethylbutylsulfonyl, 2,2-dimetiiylbutylsulfonyl, 2,3dimetiiylbutylsulfonyl, 3,3-dimethylbutylsulfonyl, 1-ethylbutylsulfonyl, 2-etiiylbutylsulfonyl, 1,1,2trimethylpropylsulfonyl, 1,2,2-trimetiiylpropylsulfonyl, 1-ethyl-1-methylpropylsulfonyl and l-ethyl-2methylpropylsulfonyl.
According to the invention, heteroarylsulfonyl denotes optionally substituted pyridylsulfonyl, pyrimidinylsulfonyl, pyrazinylsulfonyl or optionally substituted polycyclic heteroarylsulfonyl, here in particular optionally substituted quinolinylsulfonyl, for example substituted by fluorine, chlorine, bromine, iodine, cyano, nitro, alkyl, haloalkyl, haloalkoxy, amino, alkylamino, alkylcarbonylamino, dialkylamino or alkoxy groups.
According to the invention, alkyltitio - alone or as part of a chemical group - denotes straight-chain or branched S-alkyl, preferably having 1 to 8 or 1 to 6 carbon atoms, such as (Ci-Cio)-, (Ci-Ce)- or (C1-C4)alkylthio, for example (but not limited to) (Ci-Cej-alkyltitio such as metiiyltitio, ethyltitio, propyltitio, 1
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PCT/EP2017/082832 methylethylthio, butylthio, 1 -methylpropylthio, 2-methylpropylthio, 1,1 -dimethylethylthio, pentylthio,
-methylbutylthio, 2-methylbutyhhio, 3-methylbutylthio, 1,1 -dimethylpropylthio, 1,2dimethylpropylthio, 2,2-dimethylpropylthio, 1 -ethylpropylthio, hexylthio, 1 -methylpentylthio, 2methylpentylthio, 3-methylpentylthio, 4-methylpentyhhio, 1,1 -dimethylbutylthio, 1,2-dimethylbutyhhio,
1.3- dimethylbutyhhio, 2,2-dimethylbutyhhio, 2,3-dimethylbutylthio, 3,3-dimethylbutyhhio, 1ethylbutylthio, 2-ethylbutylthio, 1,1,2-trimethylpropylthio, 1,2,2-trimethylpropyhhio, 1 -ethyl-1 methylpropylthio and 1 -ethyl-2-methylpropylthio.
According to the invention, “alkenylthio” denotes an alkenyl radical bonded via a sulfur atom, alkynylthio denotes an alkynyl radical attached via a sulfur atom, cycloalkylthio denotes a cycloalkyl radical attached via a sulfur atom, and cycloalkenylthio denotes a cycloalkenyl radical attached via a sulfur atom.
According to the invention, “alkylsulfinyl (alkyl-S(=O)-)”, unless defined differently elsewhere, denotes alkyl radicals which are attached to the skeleton via -S(=O)-, such as (Ci-Cio)-, (Ci-Ce)- or (C1-C4)alkylsulfinyl, for example (but not limited to) (Ci-Cej-alkylsulfinyl such as methylsulfinyl, ethylsulfinyl, propylsulfinyl, 1-methylethylsulfinyl, butylsulfinyl, 1-methylpropylsulfinyl, 2-methylpropylsulfinyl,
1.1- dimethylethylsulfinyl, pentylsulfinyl, 1-methylbutylsulfinyl, 2-methylbutylsulfinyl, 3methylbutylsulfinyl, 1,1 -dimethylpropylsulfinyl, 1,2-dimethylpropylsulfinyl, 2,2dimethylpropylsulfinyl, 1-ethylpropylsulfinyl, hexylsulfinyl, 1-methylpentylsulfinyl, 2methylpentylsulfinyl, 3-methylpentylsulfinyl, 4-methylpentylsulfinyl, 1,1-dimethylbutylsulfinyl, 1,2dimethylbutylsulfinyl, 1,3-dimethylbutylsulfinyl, 2,2-dimethylbutylsulfinyl, 2,3-dimethylbutylsulfinyl,
3.3- dimethylbutylsulfinyl, 1 -ethylbutylsulfinyl, 2-ethylbutylsulfinyl, 1,1,2-trimethylpropylsulfinyl, 1,2,2-ttimethylpropylsulfinyl, 1-ethyl-1-methylpropylsulfinyl and 1-ethyl-2-methylpropylsulfinyl.
Analogously, “alkenylsulfinyl” and “alkynylsulfinyl” are defined in accordance with the invention as alkenyl and alkynyl radicals, respectively, which are attached to the skeleton via -S(=O)-, such as (C2C10)-, (C2-C6)- or (C2-C4)-alkenylsulfinyl or (C3-C10)-, (C3-C6)- or (C3-C4)-alkynylsulfinyl.
Analogously, “alkenylsulfonyl” and “alkynylsulfonyl” are defined in accordance with the invention as alkenyl and alkynyl radicals, respectively, which are attached to the skeleton via -S(=O)2-, such as (C2C10)-, (C2-C6)- or (C2-C4)-alkenylsulfonyl or (C3-C10)-, (C3-C6)- or (C3-C4)-alkynylsulfonyl.
“Alkoxy” denotes an alkyl radical bonded via an oxygen atom, for example (but not limited to) (Ci-Ce)alkoxy such as methoxy, ethoxy, propoxy, 1-methylethoxy, butoxy, 1-methylpropoxy, 2-methylpropoxy,
1.1- dimethylethoxy, pentoxy, 1-methylbutoxy, 2-methylbutoxy, 3-methylbutoxy, 1,1-dimethylpropoxy,
1.2- dimethylpropoxy, 2,2-dimethylpropoxy, 1 -ethylpropoxy, hexoxy, 1 -methylpentoxy, 2
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“Cycloalkyloxy” denotes a cycloalkyl radical attached via an oxygen atom and cycloalkenyloxy denotes a cycloalkenyl radical attached via an oxygen atom.
According to the invention, “alkylcarbonyl” (alkyl-C(=O)-), unless defined differently elsewhere, represents alkyl radicals attached to the skeleton via -C(=O)-, such as (C1-C10)-, (Ci-Ce)- or (C1-C4)alkylcarbonyl. Here, the number of the carbon atoms refers to the alkyl radical in the alkylcarbonyl group.
Analogously, “alkenylcarbonyl” and “alkynylcarbonyl”, unless defined differently elsewhere, in accordance with the invention, respectively represent alkenyl and alkynyl radicals attached to the skeleton via -0(=0)-, such as (C2-C10)-, (C2-C6)- or (C2-C4)-alkenylcarbonyl and (C2-C10)-, (C2-C6)- or (C2-C4)-alkynylcarbonyl. Here, the number of the carbon atoms refers to the alkenyl or alkynyl radical in the alkenyl or alkynyl group.
“Alkoxycarbonyl (alkyl-O-C(=O)-),” unless defined differently elsewhere: alkyl radicals attached to the skeleton via -0-0(=0)-, such as (C1-C10)-, (Ci-Ce)- or (Ci-C4)-alkoxycarbonyl. Here, the number of the carbon atoms refers to the alkyl radical in the alkoxycarbonyl group. Analogously, “alkenyloxycarbonyl” and “alkynyloxycarbonyl”, unless defined differently elsewhere, in accordance with the invention, respectively represent alkenyl and alkynyl radicals attached to the skeleton via -O0(=0)-, such as (C2-C10)-, (C2-C6)- or (C2-C4)-alkenyloxycarbonyl and (C3-C10)-, (C3-C6)- or (C3-C4)alkynyloxycarbonyl. Here, the number of the carbon atoms refers to the alkenyl or alkynyl radical in the alkenyloxycarbonyl or alkynyloxycarbonyl group.
According to the invention, the term “alkylcarbonyloxy” (alkyl-C(=O)-O-), unless defined differently elsewhere, represents alkyl radicals attached to the skeleton via the oxygen of a carbonyloxy group (C(=O)-O-), such as (C1-C10)-, (Ci-Ce)- or (Ci-C4)-alkylcarbonyloxy. Here, the number of the carbon atoms refers to the alkyl radical in the alkylcarbonyloxy group.
Analogously, “alkenylcarbonyloxy” and “alkynylcarbonyloxy” are defined in accordance with the invention as alkenyl and alkynyl radicals, respectively, attached to the skeleton via the oxygen of (WO 2018/114596
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0(=0)-0-), such as (C2-C10)-, (C2-C6)- or (C2-C4)-alkenylcarbonyloxy or (C2-C10)-, (C2-C6)- or (C2-C4)alkynylcarbonyloxy. Here, the number of the carbon atoms refers to the alkenyl or alkynyl radical in the alkenyl- or alkynylcarbonyloxy group respectively.
In short forms such as C(O)R12, C(O)OR12, OC(O)NR10R11 or C(O)NR10R11, the short form O shown in brackets represents an oxygen atom attached to the adjacent carbon atom via a double bond.
In short forms such as OC(S)OR12, OC(S)SR13, OC(S)NR10Rn, the short form S shown in brackets represents a sulfur atom attached to the adjacent carbon atom via a double bond.
The term aryl denotes an optionally substituted mono-, bi- or polycyclic aromatic system having preferably 6 to 14, especially 6 to 10, ring carbon atoms, for example phenyl, naphthyl, anthryl, phenanthrenyl and the like, preferably phenyl.
The term optionally substituted aryl also embraces polycyclic systems, such as tetrahydronaphthyl, indenyl, indanyl, fluorenyl, biphenylyl, where the bonding site is on the aromatic system. In systematic terms, aryl is generally also encompassed by the term optionally substituted phenyl. Preferred aryl substituents here are, for example, hydrogen, halogen, alkyl, cycloalkyl, cycloalkylalkyl, cycloalkenyl, halocycloalkyl, alkenyl, alkynyl, aryl, arylalkyl, arylalkenyl, heteroaryl, heteroarylalkyl, heterocyclyl, heterocyclylalkyl, alkoxyalkyl, alkyltitio, haloalkyltitio, haloalkyl, alkoxy, haloalkoxy, cycloalkoxy, cycloalkylalkoxy, aryloxy, heteroraryloxy, alkoxyalkoxy, alkynylalkoxy, alkenyloxy, bisalkylaminoalkoxy, tris-[alkyl]silyl, bis-[alkyl]arylsilyl, bis-[alkyl]alkylsilyl, tris-[alkyl]silylalkynyl, arylalkynyl, heteroarylalkynyl, alkylalkynyl, cycloalkylalkynyl, haloalkylalkynyl, heterocyclyl-Nalkoxy, nitro, cyano, amino, alkylamino, bis-alkylamino, alkylcarbonylamino, cycloalkylcarbonylamino, arylcarbonylamino, alkoxycarbonylamino, alkoxycarbonylalkylamino, arylalkoxycarbonylalkylamino, hydroxycarbonyl, alkoxycarbonyl, aminocarbonyl, alkylaminocarbonyl, cycloalkylaminocarbonyl, bisalkylaminocarbonyl, heteroarylalkoxy, arylalkoxy.
A heterocyclic radical (heterocyclyl) contains at least one heterocyclic ring (=carbocyclic ring in which at least one carbon atom has been replaced by a heteroatom, preferably by a heteroatom from the group of N, O, S, P) which is saturated, unsaturated, partially saturated or heteroaromatic and may be unsubstituted or substituted, in which case the bonding site is localized on a ring atom. If the heterocyclyl radical or the heterocyclic ring is optionally substituted, it may be fused to other carbocyclic or heterocyclic rings. In the case of optionally substituted heterocyclyl, polycyclic systems are also included, for example 8-azabicyclo[3.2.1]octanyl, 8-azabicyclo[2.2.2]octanyl or 1azabicyclo[2.2.1]heptyl. Optionally substituted heterocyclyl also includes spirocyclic systems, such as, for example, l-oxa-5-aza-spiro[2.3]hexyl. Unless defined otherwise, the heterocyclic ring preferably
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PCT/EP2017/082832 contains 3 to 9 ring atoms, in particular 3 to 6 ring atoms, and one or more, preferably 1 to 4, in particular 1, 2 or 3 heteroatoms in the heterocyclic ring, preferably from the group N, O and S, where, however, two oxygen atoms must not be directly adjacent to one another, for example having one heteroatom from the group consisting of N, O and S 1- or 2- or 3-pyrrolidinyl, 3,4-dihydro-2H-pyrrol-2or -3-yl, 2,3-dihydro-lH-pyrrol-l- or -2- or -3- or -4- or -5-yl; 2,5-dihydro-lH-pyrrol-l- or -2- or -3-yl,
1- or 2- or 3- or 4-piperidinyl; 2,3,4,5-tetrahydropyridin-2- or -3- or -4- or -5-yl or -6-yl; 1,2,3,6tetrahydropyridin-1 - or -2- or -3- or -4- or -5- or -6-yl; 1,2,3,4-tetrahydropyridin-l- or -2- or -3- or -4- or -5- or -6-yl; 1,4-dihydropyridin-l- or -2- or -3- or -4-yl; 2,3-dihydropyridin-2- or -3- or -4- or -5- or -6yl; 2,5-dihydropyridin-2- or -3- or -4- or -5- or -6-yl, 1- or 2- or 3- or 4-azepanyl; 2,3,4,5-tetrahydro-lHazepin-1- or -2- or -3- or -4- or -5- or -6- or -7-yl; 2,3,4,7-tetrahydro-lH-azepin-l- or -2- or -3- or -4- or -5- or -6- or -7-yl; 2,3,6,7-tetrahydro-lH-azepin-l- or -2- or -3- or -4-yl; 3,4,5,6-tetrahydro-2H-azepin-2or -3- or -4- or -5- or -6- or -7-yl; 4,5-dihydro-lH-azepin-l- or -2- or -3- or -4-yl; 2,5-dihydro-lHazepin-1- or -2- or -3- or -4- or -5- or -6- or -7-yl; 2,7-dihydro-lH-azepin-l- or -2- or -3- or -4-yl; 2,3dihydro-lH-azepin-1- or -2- or -3- or -4- or -5- or -6- or -7-yl; 3,4-dihydro-2H-azepin-2- or -3- or -4- or -5- or -6- or -7-yl; 3,6-dihydro-2H-azepin-2- or -3- or -4- or -5- or -6- or -7-yl; 5,6-dihydro-2H-azepin-2or -3- or -4- or -5- or -6- or -7-yl; 4,5-dihydro-3H-azepin-2- or -3- or -4- or -5- or -6- or -7-yl; 1Hazepin-1- or -2- or -3- or -4- or -5- or -6- or -7-yl; 2H-azepin-2- or -3- or -4- or -5- or -6- or -7-yl; 3Hazepin-2- or -3- or -4- or -5- or -6- or -7-yl; 4H-azepin-2- or -3- or -4- or -5- or -6- or -7-yl, 2- or 3oxolanyl (= 2- or 3-tetrahydrofuranyl); 2,3-dihydrofuran-2- or -3- or -4- or -5-yl; 2,5-dihydrofuran-2- or -3-yl, 2- or 3- or 4-oxanyl (= 2- or 3- or 4-tetrahydropyranyl); 3,4-dihydro-2H-pyran-2- or -3- or -4- or -
5- or -6-yl; 3,6-dihydro-2H-pyran-2- or -3-or -4- or -5- or -6-yl; 2H-pyran-2- or -3- or -4- or -5- or -6-yl; 4H-pyran-2- or -3- or -4-yl, 2- or -3- or -4-oxepanyl; 2,3,4,5-tetrahydrooxepin-2- or -3- or -4- or -5- or -
6- or -7-yl; 2,3,4,7-tetrahydrooxepin-2- or -3- or -4- or -5- or -6- or -7-yl; 2,3,6,7-tetrahydrooxepin-2- or -3- or -4-yl; 2,3-dihydrooxepin-2- or -3- or -4- or -5- or -6- or -7-yl; 4,5-dihydrooxepin-2- or -3- or -4-yl;
2,5-dihydrooxepin-2- or -3- or -4- or -5- or -6- or -7-yl; oxepin-2- or -3- or -4- or -5- or -6- or -7-yl; 2- or
3-tetrahydrothiophenyl; 2,3-dihydrothiophen-2- or -3- or -4- or -5-yl; 2,5-dihydrothiophen-2- or -3-yl; tetrahydro-2H-thiopyran-2- or -3- or -4-yl; 3,4-dihydro-2H-thiopyran-2- or -3- or -4- or -5- or -6-yl; 3,6dihydro-2H-thiopyran-2- or -3- or -4- or -5- or -6-yl; 2H-thiopyran-2- or -3- or -4- or -5- or -6-yl; 4Hthiopyran-2- or -3- or -4-yl. Preferred 3-membered and 4-membered heterocycles are, for example, 1- or
2- aziridinyl, oxiranyl, thiiranyl, 1- or 2- or 3-azetidinyl, 2- or 3-oxetanyl, 2- or 3-thietanyl, 1,3-dioxetan-
2-yl. Further examples of heterocyclyl are a partially or fully hydrogenated heterocyclic radical having two heteroatoms from the group of N, O and S, for example 1- or 2- or 3- or 4-pyrazolidinyl; 4,5dihydro-3H-pyrazol-3- or -4- or -5-yl; 4,5-dihydro-lH-pyrazol-l- or -3- or -4- or -5-yl; 2,3-dihydro-1Hpyrazol-1- or -2- or -3- or -4- or -5-yl; 1- or -2- or -3- or -4-imidazolidinyl; 2,3-dihydro-lH-imidazol-1or -2- or -3- or -4-yl; 2,5-dihydro-lH-imidazol-l- or -2- or -4- or -5-yl; 4,5-dihydro-lH-imidazol-l- or -
2- or -4- or -5-yl; hexahydropyridazin-1 - or -2- or -3- or -4-yl; 1,2,3,4-tetrahydropyridazin-l- or -2- or -
3- or -4- or -5- or -6-yl; 1,2,3,6-tetrahydropyridazin-l- or -2- or -3- or -4- or -5- or -6-yl; 1,4,5,6
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4- yl; 1,6-dihydropyridazin-1 - or -3- or -4- or -5- or -6-yl; hexahydropyrimidin-1 - or -2- or -3- or -4-yl;
1.4.5.6- tetrahydropyrimidin-l- or -2- or -4- or -5- or -6-yl; l,2,5,6-tetrahydropyrimidin-l- or -2- or -4- or -5- or -6-yl; l,2,3,4-tetrahydropyrimidin-l- or -2- or -3- or -4- or -5- or -6-yl; 1,6-dihydropyrimidin-l- or -2- or -4- or -5- or -6-yl; 1,2-dihydropyrimidin-l- or -2- or -4- or -5- or -6-yl; 2,5-dihydropyrimidin-2- or -4- or -5-yl; 4,5-dihydropyrimidin- 4- or -5- or -6-yl; 1,4-dihydropyrimidin-l- or -2- or -4- or -5- or -6yl; 1- or -2- or -3-piperazinyl; 1,2,3,6-tetrahydropyrazin-l- or -2- or -3- or -5- or -6-yl; 1,2,3,4tetrahydropyrazin-1 - or -2- or -3- or -4- or -5- or -6-yl; 1,2-dihydropyrazin-l- or -2- or -3- or -5- or -6-yl;
1,4-dihydropyrazin-1 - or -2- or -3-yl; 2,3-dihydropyrazin-2- or -3- or -5- or -6-yl; 2,5-dihydropyrazin-2or -3-yl; l,3-dioxolan-2- or -4- or -5-yl; l,3-dioxol-2- or -4-yl; l,3-dioxan-2- or -4- or -5-yl; 4H-1,3dioxin-2- or -4- or -5- or -6-yl; l,4-dioxan-2- or -3- or -5- or -6-yl; 2,3-dihydro-l,4-dioxin-2- or -3- or -
5- or -6-yl; l,4-dioxin-2- or -3-yl; l,2-dithiolan-3- or -4-yl; 3H-l,2-dithiol-3- or -4- or -5-yl; 1,3dithiolan-2- or -4-yl; 1,3-dithiol-2- or -4-yl; l,2-dithian-3- or -4-yl; 3,4-dihydro-l,2-dithiin-3- or -4- or -
5- or -6-yl; 3,6-dihydro-l,2-dithiin-3- or -4-yl; l,2-dithiin-3- or -4-yl; l,3-dithian-2- or -4- or -5-yl; 4H- l,3-dithiin-2- or -4- or -5- or -6-yl; isoxazolidin-2- or -3- or -4- or -5-yl; 2,3-dihydroisoxazol-2- or -3- or -4- or -5-yl; 2,5-dihydroisoxazol-2- or -3- or -4- or -5-yl; 4,5-dihydroisoxazol-3- or -4- or -5-yl; 1,3oxazolidin-2- or -3- or -4- or -5-yl; 2,3-dihydro-l,3-oxazol-2- or -3- or -4- or -5-yl; 2,5-dihydro-l,3oxazol-2- or -4- or -5-yl; 4,5-dihydro-l,3-oxazol-2- or -4- or -5-yl; l,2-oxazinan-2- or -3- or -4- or -5- or -6-yl; 3,4-dihydro-2H-l,2-oxazin-2- or -3- or -4- or -5- or -6-yl; 3,6-dihydro-2H-l,2-oxazin-2- or -3- or -
4- or -5- or -6-yl; 5,6-dihydro-2H-l,2-oxazin-2- or -3- or -4- or -5- or -6-yl; 5,6-dihydro-4H-l,2-oxazin-
3- or -4- or -5- or -6-yl; 2H-l,2-oxazin-2- or -3- or -4- or -5- or -6-yl; 6H-l,2-oxazin-3- or -4- or -5- or -
6- yl; 4H-l,2-oxazin-3- or -4- or -5- or -6-yl; l,3-oxazinan-2- or -3- or -4- or -5- or -6-yl; 3,4-dihydro2H-l,3-oxazin-2- or -3- or -4- or -5- or -6-yl; 3,6-dihydro-2H-l,3-oxazin-2- or -3- or -4- or -5- or -6-yl;
5.6- dihydro-2H-l,3-oxazin-2- or -4- or -5- or -6-yl; 5,6-dihydro-4H-l,3-oxazin-2- or -4- or -5- or -6-yl; 2H-l,3-oxazin-2- or -4- or -5- or -6-yl; 6H-l,3-oxazin-2- or -4- or -5- or -6-yl; 4H-l,3-oxazin-2- or -4or -5- or -6-yl; morpholin-2- or -3- or -4-yl; 3,4-dihydro-2H-l,4-oxazin-2- or -3- or -4- or -5- or -6-yl;
3.6- dihydro-2H-l,4-oxazin-2- or -3- or -5- or -6-yl; 2H-l,4-oxazin-2- or -3- or -5- or -6-yl; 4H-1,4oxazin-2- or -3-yl; l,2-oxazepan-2- or -3- or -4- or -5- or -6- or -7-yl; 2,3,4,5-tetrahydro-l,2-oxazepin-2or -3- or -4- or -5- or -6- or -7-yl; 2,3,4,7-tetrahydro-l,2-oxazepin-2- or -3- or -4- or -5- or -6- or -7-yl; 2,3,6,7-tetrahydro-l,2-oxazepin-2- or -3- or -4- or -5- or -6- or -7-yl; 2,5,6,7-tetrahydro-l,2-oxazepin-2or -3- or -4- or -5- or -6- or -7-yl; 4,5,6,7-tetrahydro-l,2-oxazepin-3- or -4- or -5- or -6- or -7-yl; 2,3dihydro-l,2-oxazepin-2- or -3- or -4- or -5- or -6- or -7-yl; 2,5-dihydro-l,2-oxazepin-2- or -3- or -4- or -
5- or -6- or -7-yl; 2,7-dihydro-l,2-oxazepin-2- or -3- or -4- or -5- or -6- or -7-yl; 4,5-dihydro-l,2oxazepin-3- or -4- or -5- or -6- or -7-yl; 4,7-dihydro-l,2-oxazepin-3- or -4- or -5- or -6- or -7-yl; 6,7dihydro-l,2-oxazepin-3- or -4- or -5- or -6- or -7-yl; l,2-oxazepin-3- or -4- or -5- or -6- or -7-yl; 1,3oxazepan-2- or -3- or -4- or -5- or -6- or -7-yl; 2,3,4,5-tetrahydro-l,3-oxazepin-2- or -3- or -4- or -5- or WO 2018/114596
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6- or -7-yl; 2,3,4,7-tetrahydro-l,3-oxazepin-2- or -3- or -4- or -5- or -6- or -7-yl; 2,3,6,7-tetrahydro-l,3oxazepin-2- or -3- or -4- or -5- or -6- or -7-yl; 2,5,6,7-tetrahydro-l,3-oxazepin-2- or -4- or -5- or -6- or -
7- yl; 4,5,6,7-tetrahydro-l,3-oxazepin-2- or -4- or -5- or -6- or -7-yl; 2,3-dihydro-l,3-oxazepin-2- or -3or -4- or -5- or -6- or -7-yl; 2,5-dihydro-l,3-oxazepin-2- or -4- or -5- or -6- or -7-yl; 2,7-dihydro-l,3oxazepin-2- or -4- or -5- or -6- or -7-yl; 4,5-dihydro-l,3-oxazepin-2- or -4- or -5- or -6- or -7-yl; 4,7dihydro-l,3-oxazepin-2- or -4- or -5- or -6- or -7-yl; 6,7-dihydro-l,3-oxazepin-2- or -4- or -5- or -6- or -
7-yl; l,3-oxazepin-2- or -4- or -5- or -6- or -7-yl; l,4-oxazepan-2- or -3- or -5- or -6- or -7-yl; 2,3,4,5tetrahydro-1,4-oxazepin-2- or -3- or -4- or -5- or -6- or -7-yl; 2,3,4,7-tetrahydro-l,4-oxazepin-2- or -3or -4- or -5- or -6- or -7-yl; 2,3,6,7-tetrahydro-l,4-oxazepin-2- or -3- or -5- or -6- or -7-yl; 2,5,6,7tetrahydro-1,4-oxazepin-2- or -3- or -5- or -6- or -7-yl; 4,5,6,7-tetrahydro-l,4-oxazepin-2- or -3- or -4or -5- or -6- or -7-yl; 2,3-dihydro-l,4-oxazepin-2- or -3- or -5- or -6- or -7-yl; 2,5-dihydro-l,4-oxazepin-
2- or -3- or -5- or -6- or -7-yl; 2,7-dihydro-l,4-oxazepin-2- or -3- or -5- or -6- or -7-yl; 4,5-dihydro-l,4oxazepin-2- or -3- or -4- or -5- or -6- or -7-yl; 4,7-dihydro-l,4-oxazepin-2- or -3- or -4- or -5- or -6- or -
7-yl; 6,7-dihydro-l,4-oxazepin-2- or -3- or -5- or -6- or -7-yl; l,4-oxazepin-2- or -3- or -5- or -6- or -Ίyl; isothiazolidin-2- or -3- or -4- or -5-yl; 2,3-dihydroisothiazol-2- or -3- or -4- or -5-yl; 2,5dihydroisothiazol-2- or -3- or -4- or -5-yl; 4,5-dihydroisothiazol-3- or -4- or -5-yl; l,3-thiazolidin-2- or -
3- or -4- or -5-yl; 2,3-dihydro-l,3-thiazol-2- or -3- or -4- or -5-yl; 2,5-dihydro-l,3-thiazol-2- or -4- or -5yl; 4,5-dihydro-l,3-thiazol-2- or -4- or -5-yl; l,3-thiazinan-2- or -3- or -4- or -5- or -6-yl; 3,4-dihydro2H-l,3-thiazin-2- or -3- or -4- or -5- or -6-yl; 3,6-dihydro-2H-l,3-thiazin-2- or -3- or -4- or -5- or -6-yl;
5,6-dihydro-2H-l,3-thiazin-2- or -4- or -5- or -6-yl; 5,6-dihydro-4H-l,3-thiazin-2- or -4- or -5- or -6-yl; 2H-l,3-thiazin-2- or -4- or -5- or -6-yl; 6H-l,3-thiazin-2- or -4- or -5- or -6-yl; 4H-l,3-thiazin-2- or -4or -5- or -6-yl. Further examples of heterocyclyl are a partially or fully hydrogenated heterocyclic radical having 3 heteroatoms from the group of N, O and S, for example l,4,2-dioxazolidin-2- or -3- or 5-yl; l,4,2-dioxazol-3- or -5-yl; 1,4,2-dioxazinan-2- or -3- or -5- or -6-yl; 5,6-dihydro-l,4,2-dioxazin-3or -5- or -6-yl; l,4,2-dioxazin-3- or -5- or -6-yl; l,4,2-dioxazepan-2- or -3- or -5- or -6- or -7-yl; 6,7dihydro-5H-l,4,2-dioxazepin-3- or -5- or -6- or -7-yl; 2,3-dihydro-7H-l,4,2-dioxazepin-2- or -3- or -5or -6- or -7-yl; 2,3-dihydro-5H-l,4,2-dioxazepin-2- or -3- or -5- or -6- or -7-yl; 5H-l,4,2-dioxazepin-3or -5- or -6- or -7-yl; 7H-l,4,2-dioxazepin-3- or -5- or -6- or -7-yl. Structural examples of heterocycles which are optionally substituted further are also listed below:
X ZN
o Xi
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Figure AU2017379281A1_D0034
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XO -¾ xo xo
Xn -¾ ox
0? X-0
•0V XT XT xx± X
90 ΧΪ X? χΌ
XX ( '
£ 'X cp X1
X X X
XX jQi X X1·
X X X Jr)
X 09 cp
The heterocycles listed above are preferably substituted, for example, by hydrogen, halogen, alkyl, haloalkyl, hydroxyl, alkoxy, cycloalkoxy, aryloxy, alkoxyalkyl, alkoxyalkoxy, cycloalkyl,
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PCT/EP2017/082832 halocycloalkyl, aryl, arylalkyl, heteroaryl, heterocyclyl, alkenyl, alkylcarbonyl, cycloalkylcarbonyl, arylcarbonyl, heteroarylcarbonyl, alkoxycarbonyl, hydroxycarbonyl, cycloalkoxycarbonyl, cycloalkylalkoxycarbonyl, alkoxycarbonylalkyl, arylalkoxycarbonyl, arylalkoxy carbonylalkyl, alkynyl, alkynylalkyl, alkylalkynyl, trisalkylsilylalkynyl, nitro, amino, cyano, haloalkoxy, haloalkylthio, alkylthio, hydrothio, hydroxyalkyl, oxo, heteroarylalkoxy, arylalkoxy, heterocyclylalkoxy, heterocyclylalkylthio, heterocyclyloxy, heterocyclylthio, heteroaryloxy, bisalkylamino, alkylamino, cycloalkylamino, hydroxycarbonylalkylamino, alkoxycarbonylalkylamino, arylalkoxycarbonylalkylamino, alkoxycarbonylalkyl(alkyl)amino, aminocarbonyl, alkylaminocarbonyl, bisalkylaminocarbonyl, cycloalkylaminocarbonyl, hydroxycarbonylalkylaminocarbonyl, alkoxycarbonylalkylaminocarbonyl, arylalkoxycarbonylalkylaminocarbonyl.
When a base structure is substituted by one or more radicals from a list of radicals (= group) or a generically defined group of radicals, this in each case includes simultaneous substitution by a plurality of identical and/or structurally different radicals.
In the case of a partially or fully saturated nitrogen heterocycle, this may be joined to the remainder of the molecule either via carbon or via the nitrogen.
Suitable substituents for a substituted heterocyclic radical are the substituents specified further down, and additionally also oxo and thioxo. The oxo group as a substituent on a ring carbon atom is then, for example, a carbonyl group in the heterocyclic ring. As a result, lactones and lactams are preferably also included. The oxo group may also occur on the ring heteroatoms, which may exist in different oxidation states, for example in the case of N and S, and in that case form, for example, the divalent -N(O)-, S(O)- (also SO for short) and -S(O)2- (also SO2 for short) groups in the heterocyclic ring. In the case ofN(O)- and -S(O)- groups, both enantiomers in each case are included.
According to the invention, the expression heteroaryl refers to heteroaromatic compounds, i.e. fully unsaturated aromatic heterocyclic compounds, preferably 5- to 7-membered rings having 1 to 4, preferably 1 or 2, identical or different heteroatoms, preferably O, S or N. Inventive heteroaryls are, for example, lH-pyrrol-l-yl; lH-pyrrol-2-yl; lH-pyrrol-3-yl; furan-2-yl; furan-3-yl; thien-2-yl; thien-3-yl, lH-imidazol-l-yl; lH-imidazol-2-yl; lH-imidazol-4-yl; lH-imidazol-5-yl; ΙΗ-pyrazol-l-yl; 1Hpyrazol-3-yl; lH-pyrazol-4-yl; lH-pyrazol-5-yl, lH-l,2,3-triazol-l-yl, lH-l,2,3-triazol-4-yl, 1H-1,2,3triazol-5-yl, 2H-l,2,3-triazol-2-yl, 2H-l,2,3-triazol-4-yl, lH-l,2,4-triazol-l-yl, lH-l,2,4-triazol-3-yl, 4H-l,2,4-triazol-4-yl, l,2,4-oxadiazol-3-yl, l,2,4-oxadiazol-5-yl, l,3,4-oxadiazol-2-yl, 1,2,3-oxadiazol-
4-yl, l,2,3-oxadiazol-5-yl, l,2,5-oxadiazol-3-yl, azepinyl, pyridin-2-yl, pyridin-3-yl, pyridin-4-yl, pyrazin-2-yl, pyrazin-3-yl, pyrimidin-2-yl, pyrimidin-4-yl, pyrimidin-5-yl, pyridazin-3-yl, pyridazin-4yl, l,3,5-triazin-2-yl, l,2,4-triazin-3-yl, l,2,4-triazin-5-yl, 1,2,4-triazin-6-yl, l,2,3-triazin-4-yl, 1,2,3
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PCT/EP2017/082832 triazin-5-yl, 1,2,4-, 1,3,2-, 1,3,6- and 1,2,6-oxazinyl, isoxazol-3-yl, isoxazol-4-yl, isoxazol-5-yl, 1,3oxazol-2-yl, l,3-oxazol-4-yl, l,3-oxazol-5-yl, isothiazol-3-yl, isothiazol-4-yl, isothiazol-5-yl, 1,3thiazol-2-yl, l,3-thiazol-4-yl, l,3-thiazol-5-yl, oxepinyl, thiepinyl, 1,2,4-triazolonyl and 1,2,4diazepinyl, 2H-l,2,3,4-tetrazol-5-yl, lH-l,2,3,4-tetrazol-5-yl, l,2,3,4-oxatriazol-5-yl, 1,2,3,4-thiatriazol-
5-yl, l,2,3,5-oxatriazol-4-yl, l,2,3,5-thiatriazol-4-yl. The heteroaryl groups according to the invention may also be substituted by one or more identical or different radicals. If two adjacent carbon atoms are part of a further aromatic ring, the systems are fused heteroaromatic systems, such as benzofused or polyannealed heteroaromatics. Preferred examples are quinolines (e.g. quinolin-2-yl, quinolin-3-yl, quinolin-4-yl, quinolin-5-yl, quinolin-6-yl, quinolin-7-yl, quinolin-8-yl); isoquinolines (e.g. isoquinolin1-yl, isoquinolin-3-yl, isoquinolin-4-yl, isoquinolin-5-yl, isoquinolin-6-yl, isoquinolin-7-yl, isoquinolin-
8-yl); quinoxaline; quinazoline; cinnoline; 1,5-naphtiiyridine; 1,6-naphtiiyridine; 1,7-naphtiiyridine; 1,8naphthyridine; 2,6-naphtiiyridine; 2,7-naphtiiyridine; phthalazine; pyridopyrazines; pyridopyrimidines; pyridopyridazines; pteridines; pyrimidopyrimidines. Examples of heteroaryl are also 5- or 6-membered benzofused rings from the group of lH-indol-l-yl, lH-indol-2-yl, lH-indol-3-yl, lH-indol-4-yl, 1Hindol-5-yl, lH-indol-6-yl, lH-indol-7-yl, l-benzofuran-2-yl, l-benzofuran-3-yl, l-benzofuran-4-yl, 1benzofuran-5-yl, 1-benzofuran-6-yl, l-benzofuran-7-yl, l-benzotitiophen-2-yl, l-benzotitiophen-3-yl, 1benzothiophen-4-yl, l-benzotitiophen-5-yl, 1-benzothiophen-6-yl, l-benzotitiophen-7-yl, lH-indazol-1yl, lH-indazol-3-yl, lH-indazol-4-yl, lH-indazol-5-yl, lH-indazol-6-yl, lH-indazol-7-yl, 2H-indazol-2yl, 2H-indazol-3-yl, 2H-indazol-4-yl, 2H-indazol-5-yl, 2H-indazol-6-yl, 2H-indazol-7-yl, 2H-isoindol-2yl, 2H-isoindol-l-yl, 2H-isoindol-3-yl, 2H-isoindol-4-yl, 2H-isoindol-5-yl, 2H-isoindol-6-yl; 2Hisoindol-7-yl, lH-benzimidazol-l-yl, lH-benzimidazol-2-yl, lH-benzimidazol-4-yl, lH-benzimidazol-5yl, lH-benzimidazol-6-yl, lH-benzimidazol-7-yl, l,3-benzoxazol-2-yl, l,3-benzoxazol-4-yl, 1,3benzoxazol-5-yl, l,3-benzoxazol-6-yl, l,3-benzoxazol-7-yl, l,3-benzotitiazol-2-yl, l,3-benzotitiazol-4yl, l,3-benzotitiazol-5-yl, l,3-benzotitiazol-6-yl, l,3-benzotitiazol-7-yl, l,2-benzisoxazol-3-yl, 1,2benzisoxazol-4-yl, l,2-benzisoxazol-5-yl, l,2-benzisoxazol-6-yl, l,2-benzisoxazol-7-yl, 1,2benzisothiazol-3-yl, l,2-benzisotitiazol-4-yl, l,2-benzisotitiazol-5-yl, l,2-benzisotitiazol-6-yl, 1,2benzisothiazol-7-yl.
The term halogen denotes, for example, fluorine, chlorine, bromine or iodine. If the term is used for a radical, halogen denotes, for example, a fluorine, chlorine, bromine or iodine atom.
According to the invention, alkyl denotes a straight-chain or branched open-chain, saturated hydrocarbon radical which is optionally mono- or polysubstituted, and in the latter case is referred to as substituted alkyl. Preferred substituents are halogen atoms, alkoxy, haloalkoxy, cyano, alkyltitio, haloalkyltitio, amino or nitro groups, particular preference being given to methoxy, methyl, fluoroalkyl, cyano, nitro, fluorine, chlorine, bromine or iodine. The prefix “bis” also includes the combination of different alkyl radicals, e.g. methyl(etiiyl) or ethyl(methyl).
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Haloalkyl, -alkenyl and -alkynyl respectively denote alkyl, alkenyl and alkynyl partially or fully substituted by identical or different halogen atoms, for example monohaloalkyl such as CH2CH2CI, CH2CH2Br, CHCICH3, CH2CI, CH2F; perhaloalkyl such as CCI3, CC1F2, CFC12,CF2CC1F2, CF2CCIFCF3; polyhaloalkyl such as CH2CHFCI, CF2CCIFH, CF2CBrFH, CH2CF3; the term perhaloalkyl also encompasses the term perfluoroalkyl.
“Partially fluorinated alkyl” denotes a straight-chain or branched, saturated hydrocarbon which is monoor polysubstituted by fluorine, where the fluorine atoms in question may be present as substituents on one or more different carbon atoms of the straight-chain or branched hydrocarbon chain, for example CHFCH3, CH2CH2F, CH2CH2CF3, CHF2, CH2F, CHFCF2CF3.
“Partly fluorinated haloalkyl” denotes a straight-chain or branched, saturated hydrocarbon which is substituted by different halogen atoms with at least one fluorine atom, where any other halogen atoms optionally present are selected from the group consisting of fluorine, chlorine or bromine, iodine. The corresponding halogen atoms may be present as substituents on one or more different carbon atoms of the straight-chain or branched hydrocarbon chain. Partly fluorinated haloalkyl also includes full substitution of the straight or branched chain by halogen including at least one fluorine atom.
“Haloalkoxy” is, for example, OCF3, OCHF2, OCH2F, OCF2CF3, OCH2CF3 and OCH2CH2CI; this applies correspondingly to haloalkenyl and other halogen-substituted radicals.
The expression (Ci-C4)-alkyl mentioned here by way of example is a brief notation for straight-chain or branched alkyl having one to 4 carbon atoms according to the range stated for carbon atoms, i.e. encompasses the methyl, ethyl, 1 -propyl, 2-propyl, 1 -butyl, 2-butyl, 2-methylpropyl or tert-butyl radicals. General alkyl radicals with a larger specified range of carbon atoms, e.g. (Ci-C6)-alkyl, correspondingly also encompass straight-chain or branched alkyl radicals with a greater number of carbon atoms, i.e. according to the example also the alkyl radicals having 5 and 6 carbon atoms.
Unless stated specifically, preference is given to the lower carbon skeletons, for example having from 1 to 6 carbon atoms, or having from 2 to 6 carbon atoms in the case of unsaturated groups, in the case of the hydrocarbyl radicals such as alkyl, alkenyl and alkynyl radicals, including in composite radicals. Alkyl radicals, including in composite radicals such as alkoxy, haloalkyl, etc., are, for example, methyl, ethyl, n-propyl or i-propyl, η-, i-, t- or 2-butyl, pentyls, hexyls such as n-hexyl, i-hexyl and 1,3dimethylbutyl, heptyls such as n-heptyl, 1 -methylhexyl and 1,4-dimethylpentyl; alkenyl and alkynyl radicals are defined as the possible unsaturated radicals corresponding to the alkyl radicals, where at
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The term alkenyl also includes, in particular, straight-chain or branched open-chain hydrocarbon radicals having more than one double bond, such as 1,3-butadienyl and 1,4-pentadienyl, but also allenyl or cumulenyl radicals having one or more cumulated double bonds, for example allenyl (1,2propadienyl), 1,2-butadienyl and 1,2,3-pentatrienyl. Alkenyl denotes, for example, vinyl which may optionally be substituted by further alkyl radicals, for example (but not limited thereto) (C2-C6)-alkenyl such as ethenyl, 1-propenyl, 2-propenyl, 1-methylethenyl, l-butenyl, 2-butenyl, 3-butenyl, 1-methyl-1propenyl, 2-methyl-1-propenyl, 1 -metiiyl-2-propenyl, 2-methyl-2-propenyl, 1-pentenyl, 2-pentenyl, 3pentenyl, 4-pentenyl, 1-methyl-l-butenyl, 2-methyl-l-butenyl, 3-methyl-l-butenyl, 1-methyl-2-butenyl, 2-methyl-2-butenyl, 3-methyl-2-butenyl, l-metiiyl-3-butenyl, 2-methyl-3-butenyl, 3-methyl-3-butenyl, 1,1 -dimetiiyl-2-propenyl, 1,2-dimethyl-1-propenyl, 1,2-dimethyl-2-propenyl, 1-ethyl-1-propenyl, 1etiiyl-2-propenyl, 1-hexenyl, 2-hexenyl, 3-hexenyl, 4-hexenyl, 5-hexenyl, 1-methyl-1-pentenyl, 2methyl-1-pentenyl, 3-methyl-1-pentenyl, 4-methyl-1-pentenyl, 1-methyl-2-pentenyl, 2-methyl-2pentenyl, 3-methyl-2-pentenyl, 4-methyl-2-pentenyl, l-methyl-3-pentenyl, 2-methyl-3-pentenyl, 3methyl-3-pentenyl, 4-methyl-3-pentenyl, l-metiiyl-4-pentenyl, 2-methyl-4-pentenyl, 3-methyl-4pentenyl, 4-methyl-4-pentenyl, 1,1-dimethyl-2-butenyl, l,l-dimethyl-3-butenyl, 1,2-dimethyl-1-butenyl, 1,2-dimethyl-2-butenyl, 1,2-dimethyl-3-butenyl, 1,3-dimethyl-l-butenyl, l,3-dimethyl-2-butenyl, 1,3dimethyl-3-butenyl, 2,2-dimethyl-3-butenyl, 2,3-dimethyl-l-butenyl, 2,3-dimethyl-2-butenyl, 2,3dimethyl-3-butenyl, 3,3-dimethyl-l-butenyl, 3,3-dimethyl-2-butenyl, 1-ethyl-1-butenyl, l-ethyl-2butenyl, l-ethyl-3-butenyl, 2-ethyl-1-butenyl, 2-ethyl-2-butenyl, 2-ethyl-3-butenyl, 1,1,2-trimethyl-2propenyl, 1 -ethyl-1 -metiiyl-2-propenyl, 1-ethyl-2-methyl- 1-propenyl and l-etiiyl-2-metiiyl-2-propenyl.
The term alkynyl also includes, in particular, straight-chain or branched open-chain hydrocarbon radicals having more than one triple bond, or else having one or more triple bonds and one or more double bonds, for example 1,3-butatrienyl or 3-penten-l-yn-l-yl. (C2-C6)-Alkynyl denotes, for example, ethynyl, 1-propynyl, 2-propynyl, l-butynyl, 2-butynyl, 3-butynyl, 1-methyl-2-propynyl, 1-pentynyl, 2pentynyl, 3-pentynyl, 4-pentynyl, 1 -methyl-2-butynyl, l-methyl-3-butynyl, 2-methyl-3-butynyl, 3methyl-l-butynyl, l,l-dimethyl-2-propynyl, l-etiiyl-2-propynyl, 1-hexynyl, 2-hexynyl, 3-hexynyl, 4hexynyl, 5-hexynyl, 1 -methyl-2-pentynyl, l-methyl-3-pentynyl, 1-methyl-4-pentynyl, 2-methyl-3pentynyl, 2-methyl-4-pentynyl, 3-methyl-1-pentynyl, 3-methyl-4-pentynyl, 4-methyl-1-pentynyl, 4methyl-2-pentynyl, 1,1 -dimethyl-2-butynyl, 1,1-dimethyl-3 -butynyl, 1,2-dimethyl-3 -butynyl, 2,2dimethyl-3-butynyl, 3,3-dimethyl-l-butynyl, 1-ethyl-2-butynyl, l-ethyl-3-butynyl, 2-ethyl-3-butynyl and 1 -ethyl-1 -metiiyl-2-propynyl.
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The term cycloalkyl denotes a carbocyclic saturated ring system having preferably 3-8 ring carbon atoms, for example cyclopropyl, cyclobutyl, cyclopentyl or cyclohexyl, which optionally has further substitution, preferably by hydrogen, alkyl, alkoxy, cyano, nitro, alkylthio, haloalkylthio, halogen, alkenyl, alkynyl, haloalkyl, amino, alkylamino, bisalkylamino, alkoxycarbonyl, hydroxycarbonyl, arylalkoxycarbonyl, aminocarbonyl, alkylaminocarbonyl, cycloalkylaminocarbonyl. In the case of optionally substituted cycloalkyl, cyclic systems with substituents are included, also including substituents with a double bond on the cycloalkyl radical, for example an alkylidene group such as methylidene. In the case of optionally substituted cycloalkyl, polycyclic aliphatic systems are also included, for example bicyclo[1.1.0]butan-l-yl, bicyclo[1.1.0]butan-2-yl, bicyclo[2.1.0]pentan-l-yl, bicyclo[l. 1.1 ]pentan-l-yl, bicyclo[2.1,0]pentan-2-yl, bicyclo[2.1,0]pentan-5-yl, bicyclo[2.1.1 ]hexyl, bicyclo[2.2.1]hept-2-yl, bicyclo[2.2.2]octan-2-yl, bicyclo[3.2.1]octan-2-yl, bicyclo[3.2.2]nonan-2-yl, adamantan-l-yl and adamantan-2-yl, but also systems such as l,l'-bi(cyclopropyl)-l-yl, 1,1'bi(cyclopropyl)-2-yl, for example. The term (C3-C7)-cycloalkyl is a brief notation for cycloalkyl having three to 7 carbon atoms, corresponding to the range specified for carbon atoms.
In the case of substituted cycloalkyl, spirocyclic aliphatic systems are also included, for example spiro[2.2]pent-l-yl, spiro[2.3]hex-l-yl, spiro[2.3]hex-4-yl, 3-spiro[2.3]hex-5-yl, spiro[3.3]hept-l-yl, spiro[3.3]hept-2-yl.
Cycloalkenyl denotes a carbocyclic, nonaromatic, partially unsaturated ring system having preferably 4-8 carbon atoms, e.g. 1-cyclobutenyl, 2-cyclobutenyl, 1-cyclopentenyl, 2-cyclopentenyl, 3cyclopentenyl, or 1-cyclohexenyl, 2-cyclohexenyl, 3-cyclohexenyl, 1,3-cyclohexadienyl or 1,4cyclohexadienyl, also including substituents with a double bond on the cycloalkenyl radical, for example an alkylidene group such as methylidene. In the case of optionally substituted cycloalkenyl, the elucidations for substituted cycloalkyl apply correspondingly.
The term alkylidene, also, for example, in the form (Ci-Cio)-alkylidene, means the radical of a straight-chain or branched open-chain hydrocarbon radical which is attached via a double bond. Possible bonding sites for alkylidene are naturally only positions on the base structure where two hydrogen atoms can be replaced by the double bond; radicals are, for example, =CH2, =CH-CH3, =C(CH3)-CH3, =C(CH3)-C2H5 or =C(C2H5)-C2H5. Cycloalkylidene denotes a carbocyclic radical attached via a double bond.
“Cycloalkylalkyloxy” denotes a cycloalkylalkyl radical attached via an oxygen atom and “arylalkyloxy” denotes and arylalkyl radical attached via an oxygen atom.
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“Alkylthioalkyl” represents an alkylthio radical attached via an alkyl group and “alkylthioalkylthio” denotes an alkylthioalkyl radical attached via an oxygen atom.
“Arylalkoxyalkyl” represents an aryloxy radical attached via an alkyl group and “heteroaryloxyalkyl” denotes a heteroaryloxy radical attached via an alkyl group.
“Haloalkoxyalkyl” represents a haloalkoxy radical and “haloalkylthioalkyl” denotes a haloalkylthio radical, attached via an alkyl group.
“Arylalkyl” represents an aryl radical attached via an alkyl group, “heteroarylalkyl” denotes a heteroaryl radical attached via an alkyl group, and “heterocyclylalkyl” denotes a heterocyclyl radical attached via an alkyl group.
“Cycloalkylalkyl” represents a cycloalkyl radical attached via an alkyl group, for example (but not limited thereto) cyclopropylmethyl, cyclobutylmethyl, cyclopentylmethyl, cyclohexylmethyl, 1 cyclopropyleth-1 -yl, 2-cyclopropyleth-1 -yl, 1 -cyclopropylprop-1 -yl, 3 -cyclopropylprop-1 -yl.
“Arylalkenyl” represents an aryl radical attached via an alkenyl group, “heteroarylalkenyl” denotes a heteroaryl radical attached via an alkenyl group, and “heterocyclylalkenyl” denotes a heterocyclyl radical attached via an alkenyl group.
“Arylalkynyl” represents an aryl radical attached via an alkynyl group, “heteroarylalkynyl” denotes a heteroaryl radical attached via an alkynyl group, and “heterocyclylalkynyl” denotes a heterocyclyl radical attached via an alkynyl group.
According to the invention, “haloalkylthio” - on its own or as constituent part of a chemical group represents straight-chain or branched S-haloalkyl, preferably having 1 to 8, or having 1 to 6 carbon atoms, such as (Ci-Cs)-, (Ci-Ce)- or (Ci-C4)-haloalkyltitio, for example (but not limited thereto) trifluorometiiyltitio, pentafluoroetiiyltitio, difluoromethyl, 2,2-difluoroetii-l-yltitio, 2,2,2-difluoroeth-1 yltitio, 3,3,3-prop-l-yltitio.
“Halocycloalkyl” and “halocycloalkenyl” denote cycloalkyl and cycloalkenyl, respectively, which are partially or fully substituted by identical or different halogen atoms, such as F, Cl and Br, or by
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According to the invention, “trialkylsilyl” - on its own or as constituent part of a chemical group represents straight-chain or branched Si-alkyl, preferably having 1 to 8, or having 1 to 6 carbon atoms, such as tri[(Ci-Cs)-, (Ci-Ce)- or (Ci-CQ-alkylJsilyl, for example (but not limited thereto) trimethylsilyl, triethylsilyl, tri(n-propyl)silyl, tri(isopropyl)silyl, tri(n-butyl)silyl, tri(l-metiiylprop-l-yl)silyl, tri(2methylprop-1 -yl)sily 1, tri( 1,1 -dimethyletii-1 -yl)sily 1, tri(2,2-dimethyletii-1 -yl)silyl.
“Trialkylsilylalkinyl” represents a trialkylsilyl radical attached via an alkynyl group.
If the compounds can form, through a hydrogen shift, tautomers whose structure is not formally covered by the formula (I), these tautomers are nevertheless covered by the definition of the inventive compounds of the formula (I), unless a particular tautomer is under consideration. For example, many carbonyl compounds may be present both in the keto form and in the enol form, both forms being encompassed by the definition of the compound of the formula (I).
Depending on the nature of the substituents and the manner in which they are attached, the compounds of the general formula (I) may be present as stereoisomers. The formula (I) embraces all possible stereoisomers defined by the specific three-dimensional form thereof, such as enantiomers, diastereomers, Z and E isomers. If, for example, one or more alkenyl groups are present, diastereomers (Z and E isomers) may occur. If, for example, one or more asymmetric carbon atoms are present, enantiomers and diastereomers may occur. Stereoisomers can be obtained from the mixtures obtained in the preparation by customary separation methods. The chromatographic separation can be effected either on the analytical scale to find the enantiomeric excess or the diastereomeric excess, or else on the preparative scale to produce test specimens for biological testing. It is likewise possible to selectively prepare stereoisomers by using stereoselective reactions with use of optically active starting materials and/or auxiliaries. The invention thus also relates to all stereoisomers which are embraced by the general formula (I) but are not shown in their specific stereomeric form, and to mixtures thereof.
If the compounds are obtained as solids, the purification can also be carried out by recrystallization or digestion. If individual compounds (I) cannot be obtained in a satisfactory manner by the routes described below, they can be prepared by derivatization of other compounds (I).
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Suitable isolation methods, purification methods and methods for separating stereoisomers of compounds of the formula (I) are methods generally known to the person skilled in the art from analogous cases, for example by physical processes such as crystallization, chromatographic methods, in particular column chromatography and HPLC (high pressure liquid chromatography), distillation, optionally under reduced pressure, extraction and other methods, any mixtures that remain can generally be separated by chromatographic separation, for example on chiral solid phases. Suitable for preparative amounts or on an industrial scale are processes such as crystallization, for example of diastereomeric salts which can be obtained from the diastereomer mixtures using optically active acids and, if appropriate, provided that acidic groups are present, using optically active bases.
Synthesis of monosubstituted heteroarylpyrrolones of the general formula (I).
The monosubstituted heteroarylpyrrolones of the general formula (I) according to the invention can be prepared using known processes. The synthesis routes used and examined proceed from commercially available or easily preparable heteroaromatic amines and of correspondingly substituted furanones or furandiones. In the schemes which follow, the moieties Q, X, Y, W, R3 and R6 of the general formula (I) have the meanings defined above, unless exemplary, but not limiting, definitions are given. The first key intermediate prepared for the synthesis of the compounds of the general formula (I) is an optionally further-substituted heteroaromatic amine Q-NH2. By way of example, but not by way of limitation, this is illustrated by the synthesis of an optionally further-substituted 5-amino-l,2,4-isothiazole (III). To this end, a substituted nitrile is converted into the corresponding amidine (for example with ammonia) and, after halogenation with a suitable halogenating agent (for example sodium hypochlorite or bromine), converted into the desired 5-amino-l,2,4-isothiazole (Illa) by reaction with potassium thiocyanate. Alternatively, bromochlorothiadiazole (IVa) can be prepared by amination, protection of the amino group (for example with (Boc)2O, where Boc represents tert-butyloxycarbonyl), subsequent transition metal-mediated coupling reaction (with a suitable transition metal catalyst such as PdC12[PlBu2(p-NMePh)]2) and subsequent acid-mediated deprotection (for example with trifluoroacetic acid = TFA) in a suitable polar-aprotic solvent (for example dichloromethane) (cf. WO2013/091539; Bioorg. Chem. 2014, 57, 90; Org. Lett. 2009, 11, 5666; WO2009/127546). Im Scheme 1 below, R4 has the meaning defined above.
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Figure AU2017379281A1_D0035
NH
Hal=CI, NaOCI
Hal=Br, Br2
Figure AU2017379281A1_D0036
Figure AU2017379281A1_D0037
(IVa)
H2N n s-N
Figure AU2017379281A1_D0038
(hoj.b-R4
z.B. PdCI2[PtBu2(p-NMe2-Ph}]2
CsF, aq. dioxane, 80°C
KSCN
Figure AU2017379281A1_D0039
Scheme 1
The synthesis of a heteroaromatic amine Q-NH2 is furthermore described using the example of the preparation of optionally further-substituted amino-l,2,4-triazoles (cf. Scheme 2). To this end, by way of example, but not by way of limitation, a substituted orthoester is reacted with cyanamine, then cyclized with hydrazine and converted with Ν,Ν-dimetiiylformamide dimethyl acetal = DMF-DMA) into a protected amino-l,2,4-triazole which can then be converted at the ring nitrogen, using a suitable reagent (e.g. an alkyl iodide) into a suitable polar-aprotic solvent (e.g. N,N-dimethylformamide) into the corresponding N-substituted amino-l,2,4-triazole (Illb). Alternatively, a suitable nitrotriazole (IVb) can be converted by substitution of the ring nitrogen and subsequent hydrogenation using a suitable transition metal catalyst (e.g. palladium or platinum on carbon) in a suitable solvent (e.g. acetic acid or dilute hydrochloric acid) into the desired N-substituted aminotriazole (Illb) (cf. Synthesis 2003, 2001; Tetrahedron Lett. 2005, 46, 2469). In Scheme 2 below, R4 and R7have the meanings defined above.
Alkylx
Figure AU2017379281A1_D0040
Alkyl
Ο O—Alkyl Alkyl n2h„ h2o
MeOH
Figure AU2017379281A1_D0041
Figure AU2017379281A1_D0042
Figure AU2017379281A1_D0043
DMF-DMA
Dioxane, reflux r __________W RJ 7 κ N τ
1. R7I, NaH, DMF
2. HCI
3. NaOMe, THF
Scheme 2
Figure AU2017379281A1_D0044
Figure AU2017379281A1_D0045
N NO.
(IVb)
N'N
R'
Figure AU2017379281A1_D0046
Figure AU2017379281A1_D0047
N NO2 R7 r‘
Figure AU2017379281A1_D0048
jl n^nh2
R7 (lb)
Figure AU2017379281A1_D0049
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The synthesis of a heteroaromatic amine Q-NH2 can furthermore be described using the example of the preparation of optionally further-substituted aminopyrazoles (cf. Scheme 3). By reaction of an optionally substituted hydrazine or a corresponding hydrazine salt with a suitable, optionally further-substituted beta-ketonitrile (IVc) in a suitable solvent (e.g. ethanol) using a suitable base (e.g. potassium carbonate), it is possible to obtain optionally further-substituted aminopyrazoles (IIIc) (cf. J. Med. Chem. 2008, 51, 4672; J. Heterocyclic Chem. 1982, 19, 1267; WO2015/018434). In Scheme 3 below, R4, R5 and R7have the meanings defined above.
Figure AU2017379281A1_D0050
Figure AU2017379281A1_D0051
H A ,n-r5 h2n
Figure AU2017379281A1_D0052
Scheme 3
Further intermediates are monosubstituted furan-2,5-diones (V), which can also be referred to as maleic anhydrides and which can be prepared by synthesis steps known from the literature (cf. J. Chem. Soc., Perkin Trans. 1, 1982, 215; EP1426365; J. Org. Chem. 1998, 63, 2646; WO2015/018431; Tetrahedron 2012, 68, 5863; Russian J. Org. Chem. 2007, 43, 801), for example compounds (V.l) and (V.2) in Scheme 4 below in a plurality of steps from a suitable acetylenedicarboxylic ester (VI). In Scheme 4 below, X by way of example, but not by way of limitation, in each case represents C-CH3 and C-C2H5, and Y by way of example, but not by way of limitation, represents C-H.
Figure AU2017379281A1_D0053
1. NaOH, H2O, EtOH
2. HCI, H2O O
Figure AU2017379281A1_D0054
(V.1) 0 .Grignard-reaction
2. NHdCI, H2O
O
Figure AU2017379281A1_D0055
(V.2)
Scheme 4
Monosubstituted heteroarylpyrrolones of the general formula (I) can be prepared in two steps by reacting a suitable optionally substituted heteroarylamine Q-NH2 (III) with a suitable optionally furthersubstituted maleic anhydride (V) using a suitable base (e.g. pyridine) in a suitable polar-aprotic solvent (e.g. acetonitrile) or under acidic conditions using a suitable acid (e.g. acetic acid or p-toluenesulfonic
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PCT/EP2017/082832 acid in toluene as solvent) and subsequent reduction of a carbonyl group of the substituted maleimide (II) formed. The reduction can be carried out in a suitable solvent (e.g. tetrahydrofuran and methanol) with the aid of a suitable reducing agent and can lead to regioisomers if X and Y are different. Suitable reducing agents are, for example, sodium hydride, lithium aluminum hydride, sodium borohydride or other hydrogen-producing metal hydrides. Alternatively, it is also possible to perform a transition metalmediated hydrogenation (cf. CH633678, DE2247266, WO20I5/018434). Since groups X and Y are different, the reduction of the carbonyl group can afford mixtures of regioisomers; accordingly, Scheme 4 below shows both possible regioisomers to illustrate this fact. In Scheme 4 below, X, Y and Q have the meanings defined above, R3, by way of example, but not by way of limitation, represents OH and R6, 10 by way of example, but not by way of limitation, represents hydrogen. Furthermore, the general reaction sequence is described in Scheme 5 below by way of example, but not by way of limitation, using Q-13 and Q-23, where, in the case of Q-23, R4 in compounds of the general formula (I), by way of example, but not by way of limitation, represents methyl and where, in the case of Q-13, R4 of the general formula (I), by way of example, but not by way of limitation, represents tert-butyl, R5 of the general formula (I) represents methyl and R7 of the general formula (I) represents hydrogen. In each case, R1 of the general formula (I), by way of example, but not by way of limitation, represents methyl.
Figure AU2017379281A1_D0056
H2N—Q (V) (111)
1) HOAc or
2) Pyridine, MeCN
O
Figure AU2017379281A1_D0057
Figure AU2017379281A1_D0058
(II)
1)HOAc
Figure AU2017379281A1_D0059
O
Figure AU2017379281A1_D0060
Reduction
Reduction xA°
N—Q
Figure AU2017379281A1_D0061
Figure AU2017379281A1_D0062
Figure AU2017379281A1_D0063
Figure AU2017379281A1_D0064
(lib)
Figure AU2017379281A1_D0065
Scheme 5.
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Alternatively, monosubstituted heteroarylpyrrolones of the general formula (la) can be prepared starting with the reaction of a hydroxy- or bromolactone (VII) with a suitable optionally substituted heteroarylamine Q-NH2 (III) in a suitable solvent (e.g. toluene) at elevated temperature. By further reaction of the resulting intermediate (VIII) with acetic anhydride using a suitable base (e.g. pyridine) at elevated temperature, the monosubstituted heteroarylpyrrolone of the general formula (IX) having an Oacetyl group is formed, which can be converted by heating under acidic conditions (e.g. in a mixture of acetic acid and water) into the corresponding monosubstituted heteroarylpyrrolone of the general formula (la) havng a free OH group. In Scheme 6 below, X, Y and Q have the meanings defined above, R3 of the general formula (I), by way of example, but not by way of limitation, represents OH, OC(O)CH3 and R6of the general formula (I), by way of example, but not by way of limitation, represents hydrogen.
Figure AU2017379281A1_D0066
Base
Figure AU2017379281A1_D0067
Ac2O
Pyridine o
Figure AU2017379281A1_D0068
Figure AU2017379281A1_D0069
H2N—Q
Figure AU2017379281A1_D0070
NH /
Q (VIII)
AcOH h2o
Br/OH (VII) (III)
Figure AU2017379281A1_D0071
(IX)
Figure AU2017379281A1_D0072
Figure AU2017379281A1_D0073
OH (I)
Scheme 6.
If monosubstitated heteroarylpyrrolones of the general formula (I) have a free hydroxyl function, this can be acylated with suitable reagents (for example using a suitable carbonyl chloride and with the aid of a suitable base such as triethylamine in a suitable polar-aprotic solvent), sulfonylated (for example using a suitable sulfonyl chloride and with the aid of a suitable base such as triethylamine in a suitable polar-aprotic solvent), alkylated (for example using a suitable alkyl halide and with the aid of a suitable base such as potassium carbonate, cesium carbonate or sodium hydride in a suitable polar-aprotic solvent) or else into a carbonate (cf. WO2015/018434). In Scheme 7 below, X, Y and Q have the meanings defined above, R3 of the general formula (1), by way of example, but not by way of limitation, represents OH, OCH3, OSO2CH3, 00(0)0¾ and 00(0)00¾ and R6 of the general formula (I), by way of example, but not by way of limitation, represents hydrogen. For better clarity, but not by way of limitation, in Scheme 7 below only one of the two possible regioisomers of the compounds of the general formula I is shown.
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Figure AU2017379281A1_D0074
Figure AU2017379281A1_D0075
(I)
Figure AU2017379281A1_D0076
ci
EtjN, DOM
O O
Figure AU2017379281A1_D0077
KjCOj or NaH
Figure AU2017379281A1_D0078
Figure AU2017379281A1_D0079
o
Figure AU2017379281A1_D0080
Figure AU2017379281A1_D0081
Figure AU2017379281A1_D0082
Figure AU2017379281A1_D0083
Scheme 6.
Selected detailed synthesis examples for the compounds of the general formula (I) according to the invention are given below. The example numbers mentioned correspond to the numbering scheme in Tables LI to 1.116 below. The Ή NMR,13C-NMR and 19F-NMR spectroscopy data reported for the chemical examples described in the sections which follow (400 MHz for 'Il-NMR and 150 MHz for 13CNMR and 375 MHz for 19F-NMR, solvent CDC13, CD3OD or de-DMSO, internal standard: tetramethylsilane δ = 0.00 ppm), were obtained on a Broker instrument, and the signals listed have the meanings given below: br = broad; s = singlet, d = doublet, t = triplet, dd = doublet of doublets, ddd = doublet of a doublet of doublets, m = multiplet, q = quartet, quint = quintet, sext = sextet, sept = septet, dq = doublet of quartets, dt = doublet of triplets. In the case of diastereomer mixtures, either the significant signals for each of the two diastereomers are reported or the characteristic signal of the main diastereomer is reported. The abbreviations used for chemical groups have, for example, the following meanings: Me = CH3, Et = CH2CH3, ΐ-Hex = C(CH3)2CH(CH3)2, t-Bu = C(CH3)3, n-Bu = unbranched butyl, n-Pr = unbranched propyl, i-Pr = branched propyl, c-Pr = cyclopropyl, c-Hex = cyclohexyl.
Synthesis examples:
No. 1.1-162: 5-Hydroxy-4-methyl-l-(5-tert-butyl-l,2-isoxazol-3-yl)-l,5-dihydro-2H-pyrrol-2-one
Figure AU2017379281A1_D0084
Citraconic anhydride (2000 mg, 17.84 mmol, 1.0 equiv) and 3-amino-5-tert-butyl-l,2-isoxazole (2501 mg, 17.84 mmol, 1.0 equiv) were dissolved in acetic acid (50 ml) and stirred under reflux conditions for
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h. After cooling to room temperature, water, sat. sodium bicarbonate solution and ethyl acetate were added and the reaction mixture was extracted. The aqueous phase was repeatedly re-extracted vigorously with ethyl acetate, and the combined organic phases were then dried over magnesium sulfate, filtered and concentrated. Final purification by column chromatography of the resulting crude product (gradient ethyl acetate/heptane) gave 4-methyl-l-(5-tert-butyl-l,2-isoxazol-5-yl)pyrrole-2,5-dione in the form of a colorless solid (3220 mg, 77% of theory). 'H-NMR (400 MHz, CDCh δ, ppm) 6.54 (m, 1H), 6.32 (s, 1H), 2.19 (s, 3H), 1.37 (s, 9H). 4-Methyl-l-(5-tert-butyl-l,2-isoxazol-3-yl)-pyrrole-2,5-dione (480 mg, 2.05 mmol, 1.0 equiv) was dissolved in methanol (5 ml) and cooled to a temperature -30°C, and sodium borohydride (155 mg, 4.09 mmol, 2.0 equiv) was added a little at a time. The resulting reaction mixture was stirred at -30°C for 1 h and then slowly warmed to room temperature and stirred at room temperature for another 1 h. After the reaction had ended, acetic acid was added carefully to adjust the pH to 3-4, and water and ethyl acetate were added. The aqueous phase was repeatedly extracted vigorously with ethyl acetate, and the combined organic phases were then dried over magnesium sulfate, filtered and concentrated. By final purification by column chromatography (gradient ethyl acetate/heptane) of the resulting crude product, it was possible to separate 5-hydroxy-4-methyl-l-(5-tertbutyl-l,2-isoxazol-3-yl)-l,5-dihydro-2H-pyrrol-2-one from the isomeric 5-hydroxy-3-methyl-l-(5-tertbutyl-l,2-isoxazol-3-yl)-l,5-dihydro-2H-pyrrol-2-one 1.2-162 and to isolate the compound in the form of a colorless solid (155 mg, 32% of theory). 'H-NMR (400 MHz, CDCI3 δ, ppm) 6.72 (s, 1H), 5.95 (m, 1H), 5.90 (br. d, 1H), 4.44 (br. d, 1H), 2.16 (s, 3H), 1.36 (s, 9H).
No. 1.1-290: 5-Hydroxy-4-methyl-l-(3-tert-butyl-l,2-isoxazol-5-yl)-l,5-dihydro-2H-pyrrol-2-one
Figure AU2017379281A1_D0085
OH
Citraconic anhydride (2000 mg, 17.84 mmol, 1.0 equiv) and 5-amino-3-tert-butyl-1,2-isoxazole (2752 mg, 19.63 mmol, 1.1 equiv) were dissolved in acetic acid (50 ml) and stirred under reflux conditions for 8 h. After cooling to room temperature, water, sat. sodium bicarbonate solution and ethyl acetate were added and the reaction mixture was extracted. The aqueous phase was repeatedly re-extracted vigorously with ethyl acetate, and the combined organic phases were then dried over magnesium sulfate, filtered and concentrated. Final purification by column chromatography of the resulting crude product (gradient ethyl acetate/heptane) gave 4-methyl-1-(3-tert-butyl-l,2-isoxazol-5-yl)pyrrole-2,5-dione in the form of a colorless solid (3620 mg, 78% of theory). 'H-NMR (400 MHz, CDCI3 δ, ppm) 6.56 (m, 1H), 6.22 (s, 1H), 2.19 (s, 3H), 1.35 (s, 9H). 4-Methyl-1-(3-tert-butyl-l,2-isoxazol-5-yl)pyrrole-2,5-dione (3500 mg, 14.94 mmol, 1.0 equiv) was dissolved in methanol (90 ml) and cooled to a temperature -30°C, and
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PCT/EP2017/082832 sodium borohydride (790 mg, 20.92 mmol, 1.4 equiv) was added a little at a time. The resulting reaction mixture was stirred at -30°C for 1 h and then slowly warmed to room temperature and stirred at room temperature for another 1 h. After the reaction had ended, acetic acid was added carefully to adjust the pH to 3-4, and water and ethyl acetate were added. The aqueous phase was repeatedly extracted vigorously with ethyl acetate, and the combined organic phases were then dried over magnesium sulfate, filtered and concentrated. By final purification by column chromatography (gradient ethyl acetate/heptane) of the resulting crude product, it was possible to separate 5-hydroxy-4-methyl-l-(3-tertbutyl-l,2-isoxazol-5-yl)-l,5-dihydro-2H-pyrrol-2-one from the isomeric 5-hydroxy-3-methyl-l-(3-tertbutyl-l,2-isoxazol-5-yl)-l,5-dihydro-2H-pyrrol-2-one 1.2-290 and to isolate the compound in the form of a colorless solid (350 mg, 10% of theory). 'H-NMR (400 MHz, de-DMSO δ, ppm) 7.09 (br. d, 1H), 6.21 (s, 1H), 6.03 (m, 1H), 5.90 (br. d, 1H), 2.04 (s, 3H), 1.27 (s, 9H).
No. 1.1-387: 5-Hydroxy-4-methyl-l-(l,5-diphenyl-l,2-pyrazol-3-yl)-l,5-dihydro-2H-pyrrol-2-one
Citraconic anhydride (519 mg, 4.64 mmol, 1.1 equiv) and 3-amino-l,5-diphenyl-l,2-pyrazole (1000 mg, 4.21 mmol, 1.0 equiv) were dissolved in acetonitrile (20 ml), pyridine (0.14 ml, 1.69 mmol, 0.4 equiv) was added and the mixture was stirred under reflux conditions for 14 h. After cooling to room temperature, water and ethyl acetate were added and the mixture was extracted thoroughly. The aqueous phase was repeatedly re-extracted vigorously with ethyl acetate, and the combined organic phases were then dried over magnesium sulfate, filtered and concentrated. Final purification by column chromatography of the resulting crude product (gradient ethyl acetate/heptane) gave 4-methyl-l-(l,5diphenyl-l,2-pyrazol-3-yl)pyrrole-2,5-dione in the form of a colorless solid (100 mg, 7% of theory). 4Methyl-l-(l,5-diphenyl-l,2-pyrazol-3-yl)pyrrole-2,5-dione (80 mg, 0.24 mmol, 1.0 equiv) was dissolved in a mixture of methanol and tetrahydrofuran (20 ml, 1:1 mixture) and cooled to a temperature -30°C, and sodium borohydride (18 mg, 0.48 mmol, 2.0 equiv) was added. The resulting reaction mixture was stirred at -30°C for 2 h and then slowly warmed to room temperature and stirred at room temperature for another 1 h. After the reaction had ended, acetic acid was added carefully to adjust the pH to 3-4, and water and ethyl acetate were added. The aqueous phase was repeatedly extracted vigorously with ethyl acetate, and the combined organic phases were then dried over magnesium sulfate, filtered and concentrated. Final purification by column chromatography of the resulting crude product (gradient ethyl acetate/heptane) gave 5-hydroxy-4-methyl-l-(l,5-diphenyl-l,2-pyrazol-3-yl)-l,5WO 2018/114596
PCT/EP2017/082832 dihydro-2H-pyrrol-2-one in the form of a colorless solid (11 mg, 13% of theory). 'H-NMR (400 MHz, CDCh δ, ppm) 7.36-7.24 (m, 10H), 7.06 (s, 1H), 5.98 (s, 1H), 5.95 (br. d, 1H), 4.81 (br. m, 1H), 2.16 (s, 3H).
No. 1.1-451: 5-Hydroxy-4-methyl-l-(5-chloro-4-trifhioromethylpyridin-2-yl)-l,5-dihydro-2H-pyrrol-2 one
Figure AU2017379281A1_D0086
5-Ethylcarbonyloxy-4-methyl-l-(5-chloro-4-trifhioromethylpyridin-2-yl)-l,5-dihydro-2H-pyrrol-2-one (130 mg, 0.37 mmol, 1.0 equiv) and lithium hydroxide (10 mg, 0.41 mmol, 1.1 equiv) were dissolved in a mixture of tetrahydrofuran and water (9 ml, 1:1 mixture) and stirred at room temperature for 4 h. After the reaction had ended, buffer solution was added carefully to adjust the pH to 4-5, and water and ethyl acetate were added. The aqueous phase was repeatedly extracted vigorously with ethyl acetate, and the combined organic phases were then dried over magnesium sulfate, filtered and concentrated. Final purification by column chromatography of the resulting crude product (gradient ethyl acetate/heptane) gave 5-hydroxy-4-methyl-l-(5-chloro-4-trifluoromethylpyridin-2-yl)-l,5-dihydro-2H-pyrrol-2-one in the form of a colorless solid (50 mg, 46% of theory). 'H-NMR (400 MHz, CDCh δ, ppm) 8.76 (s, 1H), 8.41 (s, 1H), 6.07 (m, 1H), 5.96 (s, 1H), 4.93 (d, 1H), 2.18 (s, 3H).
No.1.1-558:5-Hydroxy-4-methyl-1-(3 -ethyl-1,2,4-thiadiazol-5-yl)-1,5 -dihydro-2H-pyrrol-2-one
Figure AU2017379281A1_D0087
Citraconic anhydride (400 mg, 3.57 mmol, 1.0 equiv), p-toluenesulfonic acid (92 mg, 0.54 mmol) and 5amino-3-ethyl-l,2,4-thiadiazole (461 mg, 3.57 mmol, 1.0 equiv) were dissolved in toluene (12 ml) and stirred under microwave conditions at a temperature of 85°C for 60 minutes. After cooling to room temperature, water, sat. sodium bicarbonate solution and ethyl acetate were added and the reaction mixture was extracted. The aqueous phase was repeatedly re-extracted vigorously with ethyl acetate, and the combined organic phases were then dried over magnesium sulfate, filtered and concentrated. Final purification by column chromatography of the resulting crude product (gradient ethyl acetate/heptane) gave 4-methyl-1-(3-ethyl-1,2,4-thiadiazol-5-yl)pyrrole-2,5-dione in the form of a colorless solid (120 mg, 15% of theory). 'H-NMR (400 MHz, CDCI3 δ, ppm) 6.67 (m, 1H), 3.04 (q, 2H), 2.25 (s, 3H), 1.40
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PCT/EP2017/082832 (t, 3H). 4-Methyl-1-(3-ethyl-1,2,4-thiadiazol-5-yl)pyrrole-2,5-dione (100 mg, 0.45 mmol, 1.0 equiv) was dissolved in a mixture of tetrahydrofuran and methanol (10 ml, 1:1) and cooled to a temperature of 30°C, and sodium borohydride (17 mg, 0.45 mmol, 1.0 equiv) was added. The resulting reaction mixture was stirred at -30°C for 2 h and then slowly warmed to room temperature. After the reaction had ended, acetic acid was added carefully to adjust the pH to 3-4, and water and ethyl acetate were added. The aqueous phase was repeatedly extracted vigorously with ethyl acetate, and the combined organic phases were then dried over magnesium sulfate, filtered and concentrated. Final purification by column chromatography of the resulting crude product (gradient ethyl acetate/heptane) gave 5-hydroxy-4methyl-l-(3-etiiyl-l,2,4-thiadiazol-5-yl)-l,5-dihydro-2H-pyrrol-2-one in the form of a colorless solid (30 mg, 30% of theory). 'H-NMR (400 MHz, CDCh δ, ppm) 6.08 (m, 1H), 6.03 (br. s, 1H), 4.77 (d, 1H), 2.92-2.86 (q, 2H), 2.23 (s, 3H), 1.37 (t, 3H).
No.1.1-560:5-Hydroxy-4-metiiyl-1-(3 -isopropyl-1,2,4-thiadiazol-5-yl)-1,5-dihydro-2H-pyrrol-2-one
OH
Citraconic anhydride (400 mg, 3.57 mmol, 1.0 equiv), p-toluenesulfonic acid (92 mg, 0.54 mmol) and 5amino-3-isopropyl-l,2,4-thiadiazole (511 mg, 3.57 mmol, 1.0 equiv) were dissolved in toluene (12 ml) and stirred under microwave conditions at a temperature of 95°C for 60 minutes. After cooling to room temperature, water, sat. sodium bicarbonate solution and ethyl acetate were added and the reaction mixture was extracted. The aqueous phase was repeatedly re-extracted vigorously with ethyl acetate, and the combined organic phases were then dried over magnesium sulfate, filtered and concentrated. Final purification by column chromatography of the resulting crude product (gradient ethyl acetate/heptane) gave 4-methyl-l-(3-isopropyl-1,2,4-thiadiazol-5-yl)pyrrole-2,5-dione in the form of a colorless solid (90 mg, 11% of theory). 'H-NMR (400 MHz, CDCI3 δ, ppm) 6.66 (m, 1H), 3.35 (sept, 1H), 2.24 (s, 3H), 1.41 (d, 6H). 4-Methyl-1-(3-isopropyl-1,2,4-thiadiazol-5-yl)pyrrole-2,5-dione (75 mg, 0.32 mmol, 1.0 equiv) was dissolved in a mixture of tetrahydrofuran and methanol (8 ml, 1:1) and cooled to a temperature of -30°C, and sodium borohydride (12 mg, 0.45 mmol, 1.0 equiv) was added. The resulting reaction mixture was stirred at -30°C for 2 h and then slowly warmed to room temperature. After the reaction had ended, acetic acid was added carefully to adjust the pH to 3-4, and water and ethyl acetate were added. The aqueous phase was repeatedly extracted vigorously with ethyl acetate, and the combined organic phases were then dried over magnesium sulfate, filtered and concentrated. Final purification by column chromatography of the resulting crude product (gradient ethyl acetate/heptane) gave 5-hydroxy-4-metiiyl-l-(3-isopropyl-l,2,4-thiadiazol-5-yl)-l,5-dihydro-2H-pyrrol-2-one in the form
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PCT/EP2017/082832 of a colorless solid (7 mg, 9% of theory). 'H-NMR (400 MHz, CDCh δ, ppm) 6.08 (m, 1H), 6.05 (d,
1H), 4.81 (d, 1H), 3.23-3.15 (sept, 1H), 2.23 (s, 3H), 1.37 (d, 6H).
No. 1.5-451: 5-Ethylcarbonyloxy-4-methyl-l-(5-chloro-4-trifluoromethylpyridin-2-yl)-l,5-dihydro-2H pyrrol-2-one
Figure AU2017379281A1_D0088
5-Hydroxy-4-methyl-2,5-dihydrofuran-2-one (300 mg, 2.63 mmol, 1.0 equiv) and 2-amino-5-chloro-4trifhioromethylpyridine (568 mg, 2.89 mmol, 1.1 equiv) were dissolved in abs. toluene (12 ml) and stirred under reflux conditions for 16 h. After cooling to room temperature, the reaction mixture was filtered off with suction and, after thorough drying, 5-(5-chloro-4-trifluoromethylpyridin-2-yl)amino-4methyl-2,5-dihydrofuran-2-one was isolated without any further purification in the form of a colorless solid (530 mg, 68% of theory).). 'H-NMR (400 MHz, de-DMSO δ, ppm) 8.43 (s, 1H), 8.36 (d, 1H), 7.06 (s, 1H), 6.78 (d, 1H), 6.15 (m, 1H), 2.07 (s, 3H). 5-(5-Chtoro-4-trifluoromethylpyridin-2-yl)amino4-methyl-2,5-dihydrofuran-2-one (250 mg, 0.85 mmol, 1.0 equiv) was dissolved in propionic anhydride (2.22 g, 20 equiv) and stirred at a temperature of 155°C for 4 h. After cooling to room temperature, the reaction mixture was filtered off with suction, and final purification by column chromatography of the resulting crude product (gradient ethyl acetate/heptane) gave 5-ethylcarbonyloxy-4-methyl-l-(5-chloro4-trifluoromethylpyridin-2-yl)-l,5-dihydro-2H-pyrrol-2-one in the form of a colorless solid (35 mg, 12% of theory). 'H-NMR (400 MHz, CDCI3 δ, ppm) 8.67 (s, 1H), 8.39 (s, 1H), 7.42 (s, 1H), 6.02 (m, 1H), 2.39-2.32 (m, 2H), 2.08 (s, 3H), 1.17 (t, 3H).
No. 1.11-162: 5-Ethoxycarbonyloxy-4-methyl-l-(5-tert-butyl-l,2-isoxazol-3-yl)-l,5-dihydro-2H-pyrrol2-one
Figure AU2017379281A1_D0089
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5-Hydroxy-4-methyl-2,5-dihydrofuran-2-one (1000 mg, 8.76 mmol, 1.0 equiv) and 3-amino-5-tertbutyl-1,2-isoxazole (1351 mg, 9.64 mmol, 1.1 equiv) were dissolved in abs. toluene (20 ml) and stirred under reflux conditions for 8 h. After cooling to room temperature, the reaction mixture was filtered off with suction and, after thorough drying, 5-(5-tert-butyl-l,2-isoxazol-3-yl)amino-4-metiiyl-2,5dihydrofuran-2-one was isolated without any further purification in the form of a colorless solid (1470 mg, 71% of theory).). 'H-NMR (400 MHz, CDCh δ, ppm) 6.12 (m, 1H), 5.96 (d, 1H), 5.65 (s, 1H), 4.95 (br. d, 1H), 2.14 (s, 3H), 1.31 (s, 9H). 5-(5-tert-Butyl-l,2-isoxazol-3-yl)amino-4-metiiyl-2,5dihydrofuran-2-one (150 mg, 0.64 mmol, 1.0 equiv) was dissolved in diethyl carbonate (1.54 ml, 20 equiv) and stirred at a temperature of 120°C for 8 h. After cooling to room temperature, the reaction mixture was filtered off with suction, and final purification by column chromatography of the resulting crude product (gradient ethyl acetate/heptane) gave 5-ethoxycarbonyloxy-4-metiiyl-1-(5-tert-butyl-1,2isoxazol-3-yl)-l,5-dihydro-2H-pyrrol-2-one in the form of a colorless solid (63 mg, 32% of theory). *HNMR (400 MHz, CDCI3 δ, ppm) 6.95 (s, 1H), 6.68 (s, 1H), 6.02 (m, 1H), 4.37-4.32 (m, 2H), 2.12 (s, 3H), 1.39 (t, 3H), 1.34 (s, 9H).
No. 1.22-162: 5-Hydroxy-3-tert-butyl-1 -(5-tert-butyl-1,2-isoxazol-3-yl)-l,5-dihydro-2H-pyrrol-2-one
OH
3-tert-Butylfuran-2,5-dione (1600 mg, 10.38 mmol, 1.0 equiv) and 3-amino-5-tert-butyl-1,2-isoxazole (1600 mg, 11.42 mmol, 1.1 equiv) were dissolved in acetic acid (40 ml) and stirred under reflux conditions for 8 h. After cooling to room temperature, water, sat. sodium bicarbonate solution and ethyl acetate were added and the reaction mixture was extracted. The aqueous phase was repeatedly reextracted vigorously with ethyl acetate, and the combined organic phases were then dried over magnesium sulfate, filtered and concentrated. Final purification by column chromatography of the resulting crude product (gradient ethyl acetate/heptane) gave 3-tert-butyl-l-(5-tert-butyl-l,2-isoxazol-5yl)pyrrole-2,5-dione in the form of a colorless solid (1550 mg, 54% of theory). 'H-NMR (400 MHz, CDCI3 δ, ppm) 6.43 (2, 1H), 6.33 (s, 1H), 1.37 (s, 9H), 1.36 (s, 9H). 3-tert-Butyl-l-(5-tert-butyl-l,2isoxazol-5-yl)pyrrole-2,5-dione (1400 mg, 5.07 mmol, 1.0 equiv) was dissolved in methanol (20 ml) and cooled to a temperature of -30°C, and sodium borohydride (2.0 equiv) was added a little at a time. The resulting reaction mixture was stirred at -30°C for 1 h and then slowly warmed to room temperature and stirred at room temperature for another 1 h. After the reaction had ended, acetic acid was added carefully to adjust the pH to 3-4, and water and ethyl acetate were added. The aqueous phase was repeatedly extracted vigorously with ethyl acetate, and the combined organic phases were then dried over
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PCT/EP2017/082832 magnesium sulfate, filtered and concentrated. By final purification by column chromatography (gradient ethyl acetate/heptane) of the resulting crude product, it was possible to separate 5-hydroxy-3-tert-butyl-
1- (5-tert-butyl-l,2-isoxazol-3-yl)-l,5-dihydro-2H-pyrrol-2-one from the isomeric 5-hydroxy-4-tertbutyl-1-(5-tert-butyl-l,2-isoxazol-3-yl)-l,5-dihydro-2H-pyrrol-2-one 1.21-162 and to isolate the compound in the form of a colorless solid (990 mg, 70% of theory). 'H-NMR (400 MHz, CDCh δ, ppm) 6.77 (s, 1H), 6.66 (s, 1H), 5.97 (br. d, 1H), 4.28 (br. d, 1H), 1.35 (s, 9H), 1.30 (s, 9H).
No. 1.26-162: 5-Ethylcarbonyloxy-3-tert-butyl-l-(5-tert-butyl-l,2-isoxazol-3-yl)-l,5-dihydro-2H-pyrrol-
2- one
Under argon, 5-hydroxy-3-tert-butyl-l-(5-tert-butyl-l,2-isoxazol-3-yl)-l,5-dihydro-2H-pyrrol-2-one (950 mg, 3.41 mmol, 1.0 equiv) was dissolved in abs. dichloromethane (75 ml), diisopropylethylamine (706 mg, 5.46 mmol, 1.6 equiv), propionyl chloride (474 mg, 5.12 mmol, 1.5 equiv) and 4dimethylaminopyridine (42 mg, 0.34 mmol, 0.1 equiv) were added and the mixture was stirred at room temperature for 2 h. This was followed by the addition of water and dichloromethane and thorough extraction. The aqueous phase was repeatedly re-extracted vigorously with dichloromethane, and the combined organic phases were then dried over magnesium sulfate, filtered and concentrated. Final purification by column chromatography of the resulting crude product (gradient ethyl acetate/heptane) gave 5-ethylcarbonyloxy-3-tert-butyl-l-(5-tert-butyl-l,2-isoxazol-3-yl)-l,5-dihydro-2H-pyrrol-2-one in the form of a colorless solid (450 mg, 39% of theory). 'H-NMR (400 MHz, CDCI3 δ, ppm) 6.90 (s, 1H), 6.75 (s, 1H), 6.71 (m, 1H), 2.52-2.34 (m, 2H), 1.34 (s, 9H), 1.29 (s, 9H), 1.17 (t, 3H).
In analogy to the preparation examples cited above and recited at the appropriate point, and taking account of the general details relating to the preparation of monosubstituted heteroarylpyrrolones, the compounds cited below are obtained. If in Table 1 a structural element is defined by a structural formula containing a broken line, this broken line means that at this position the group in question is attached to the remainder of the molecule.
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Table 1:
Figure AU2017379281A1_D0090
Table 1.1: Preferred compounds of the formula (1.1) are the compounds 1.1-1 to 1.1-708 in which Q has the meanings of Table 1 indicated in the respective row. Thus, the compounds 1.1-1 to 1.1-708 of Table
1.1 are defined by the meaning of the respective entries Nos. 1 to 708 for Q of Table 1.
No. Q
1 Q-l.l
2 Q-1.2
3 Q-1.3
4 Q-1.4
5 Q-1.5
6 Q-1.6
7 Q-1.7
8 Q-1.8
9 Q-1.9
10 Q-1.10
11 Q-1.11
12 Q-1.12
13 Q-1.13
14 Q-1.14
15 Q-1.15
16 Q-1.16
17 Q-1.17
18 Q-1.18
19 Q-1.19
20 Q-1.20
21 Q-2.1
22 Q-2.2
23 Q-2.3
24 Q-2.4
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No. Q
25 Q-2.5
26 Q-2.6
27 Q-2.7
28 Q-2.8
29 Q-2.9
30 Q-2.10
31 Q-2.11
32 Q-2.12
33 Q-2.13
34 Q-2.14
35 Q-2.15
36 Q-2.16
37 Q-2.17
38 Q-2.18
39 Q-2.19
40 Q-2.20
41 Q-3.1
42 Q-3.2
43 Q-3.3
44 Q-3.4
45 Q-3.5
46 Q-3.6
47 Q-3.7
48 Q-3.8
49 Q-3.9
50 Q-3.10
51 Q-3.11
52 Q-3.12
53 Q-3.13
54 Q-3.14
55 Q-3.15
56 Q-3.16
57 Q-3.17
58 Q-3.18
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No. Q
59 Q-3.19
60 Q-3.20
61 Q-3.21
62 Q-3.22
63 Q-3.23
64 Q-3.24
65 Q-3.25
66 Q-3.26
67 Q-3.27
68 Q-3.28
69 Q-3.29
70 Q-3.30
71 Q-4.1
72 Q-4.2
73 Q-4.3
74 Q-4.4
75 Q-4.5
76 Q-4.6
77 Q-4.7
78 Q-4.8
79 Q-4.9
80 Q-4.10
81 Q-4.11
82 Q-4.12
83 Q-4.13
84 Q-4.14
85 Q-4.15
86 Q-4.16
87 Q-4.17
88 Q-4.18
89 Q-4.19
90 Q-4.20
91 Q-5.1
92 Q-5.2
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No. Q
93 Q-5.3
94 Q-5.4
95 Q-5.5
96 Q-5.6
97 Q-5.7
98 Q-5.8
99 Q-5.9
100 Q-5.10
101 Q-5.11
102 Q-5.12
103 Q-5.13
104 Q-5.14
105 Q-5.15
106 Q-5.16
107 Q-5.17
108 Q-5.18
109 Q-5.19
110 Q-5.20
111 Q-6.1
112 Q-6.2
113 Q-6.3
114 Q-6.4
115 Q-6.5
116 Q-6.6
117 Q-6.7
118 Q-6.8
119 Q-6.9
120 Q-6.10
121 Q-6.11
122 Q-6.12
123 Q-6.13
124 Q-6.14
125 Q-6.15
126 Q-6.16
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No. Q
127 Q-6.17
128 Q-6.18
129 Q-6.19
130 Q-6.20
131 Q-6.21
132 Q-6.22
133 Q-6.23
134 Q-6.24
135 Q-6.25
136 Q-7.1
137 Q-7.2
138 Q-7.3
139 Q-7.4
140 Q-7.5
141 Q-7.6
142 Q-7.7
143 Q-7.8
144 Q-7.9
145 Q-7.10
146 Q-7.11
147 Q-7.12
148 Q-7.13
149 Q-7.14
150 Q-7.15
151 Q-7.16
152 Q-7.17
153 Q-7.18
154 Q-7.19
155 Q-7.20
156 Q-8.1
157 Q-8.2
158 Q-8.3
159 Q-8.4
160 Q-8.5
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No. Q
161 Q-8.6
162 Q-8.7
163 Q-8.8
164 Q-8.9
165 Q-8.10
166 Q-8.11
167 Q-8.12
168 Q-8.13
169 Q-8.14
170 Q-8.15
171 Q-8.16
172 Q-8.17
173 Q-8.18
174 Q-8.19
175 Q-8.20
176 Q-8.21
177 Q-8.22
178 Q-8.23
179 Q-8.24
180 Q-8.25
181 Q-8.26
182 Q-8.27
183 Q-8.28
184 Q-8.29
185 Q-8.30
186 Q-8.31
187 Q-8.32
188 Q-8.33
189 Q-8.34
190 Q-8.35
191 Q-8.36
192 Q-8.37
193 Q-8.38
194 Q-8.39
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No. Q
195 Q-8.40
196 Q-8.41
197 Q-8.42
198 Q-8.43
199 Q-8.44
200 Q-8.45
201 Q-8.46
202 Q-8.47
203 Q-8.48
204 Q-8.49
205 Q-8.50
206 Q-8.51
207 Q-8.52
208 Q-8.53
209 Q-8.54
210 Q-8.55
211 Q-8.56
212 Q-8.57
213 Q-8.58
214 Q-8.59
215 Q-8.60
216 Q-8.61
217 Q-8.62
218 Q-8.63
219 Q-8.64
220 Q-8.65
221 Q-8.66
222 Q-8.67
223 Q-8.68
224 Q-8.69
225 Q-8.70
226 Q-8.71
227 Q-8.72
228 Q-8.73
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No. Q
229 Q-8.74
230 Q-8.75
231 Q-9.1
232 Q-9.2
233 Q-9.3
234 Q-9.4
235 Q-9.5
236 Q-9.6
237 Q-9.7
238 Q-9.8
239 Q-9.9
240 Q-9.10
241 Q-9.11
242 Q-9.12
243 Q-9.13
244 Q-9.14
245 Q-9.15
246 Q-9.16
247 Q-9.17
248 Q-9.18
249 Q-9.19
250 Q-9.20
251 Q-10.1
252 Q-10.2
253 Q-10.3
254 Q-10.4
255 Q-10.5
256 Q-10.6
257 Q-10.7
258 Q-10.8
259 Q-10.9
260 Q-10.10
261 Q-10.11
262 Q-10.12
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No. Q
263 Q-10.13
264 Q-10.14
265 Q-10.15
266 Q-10.16
267 Q-10.17
268 Q-10.18
269 Q-10.19
270 Q-10.20
271 Q-ll.l
272 Q-11.2
273 Q-11.3
274 Q-11.4
275 Q-11.5
276 Q-11.6
277 Q-11.7
278 Q-11.8
279 Q-11.9
280 Q-11.10
281 Q-ll.ll
282 Q-11.12
283 Q-11.13
284 Q-11.14
285 Q-11.15
286 Q-12.1
287 Q-12.2
288 Q-12.3
289 Q-12.4
290 Q-12.5
291 Q-12.6
292 Q-12.7
293 Q-12.8
294 Q-12.9
295 Q-12.10
296 Q-12.11
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No. Q
297 Q-12.12
298 Q-12.13
299 Q-12.14
300 Q-12.15
301 Q-12.16
302 Q-12.17
303 Q-12.18
304 Q-12.19
305 Q-12.20
306 Q-12.21
307 Q-12.22
308 Q-12.23
309 Q-12.24
310 Q-12.25
311 Q-13.1
312 Q-13.2
313 Q-13.3
314 Q-13.4
315 Q-13.5
316 Q-13.6
317 Q-13.7
318 Q-13.8
319 Q-13.9
320 Q-13.10
321 Q-13.11
322 Q-13.12
323 Q-13.13
324 Q-13.14
325 Q-13.15
326 Q-13.16
327 Q-13.17
328 Q-13.18
329 Q-13.19
330 Q-13.20
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No. Q
331 Q-13.21
332 Q-13.22
333 Q-13.23
334 Q-13.24
335 Q-13.25
336 Q-13.26
337 Q-13.27
338 Q-13.28
339 Q-13.29
340 Q-13.30
341 Q-13.31
342 Q-13.32
343 Q-13.33
344 Q-13.34
345 Q-13.35
346 Q-13.36
347 Q-13.37
348 Q-13.38
349 Q-13.39
350 Q-13.40
351 Q-13.41
352 Q-13.42
353 Q-13.43
354 Q-13.44
355 Q-13.45
356 Q-13.46
357 Q-13.47
358 Q-13.48
359 Q-13.49
360 Q-13.50
361 Q-13.51
362 Q-13.52
363 Q-13.53
364 Q-13.54
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No. Q
365 Q-13.55
366 Q-13.56
367 Q-13.57
368 Q-13.58
369 Q-13.59
370 Q-13.60
371 Q-13.61
372 Q-13.62
373 Q-13.63
374 Q-13.64
375 Q-13.65
376 Q-13.66
377 Q-13.67
378 Q-13.68
379 Q-13.69
380 Q-13.70
381 Q-13.71
382 Q-13.72
383 Q-13.73
384 Q-13.74
385 Q-13.75
386 Q-13.76
387 Q-13.77
388 Q-13.78
389 Q-13.79
390 Q-13.80
391 Q-14.1
392 Q-14.2
393 Q-14.3
394 Q-14.4
395 Q-14.5
396 Q-14.6
397 Q-14.7
398 Q-14.8
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No. Q
399 Q-14.9
400 Q-14.10
401 Q-14.11
402 Q-14.12
403 Q-14.13
404 Q-14.14
405 Q-14.15
406 Q-14.16
407 Q-14.17
408 Q-14.18
409 Q-14.19
410 Q-14.20
411 Q-15.1
412 Q-15.2
413 Q-15.3
414 Q-15.4
415 Q-15.5
416 Q-15.6
417 Q-15.7
418 Q-15.8
419 Q-15.9
420 Q-15.10
421 Q-15.11
422 Q-15.12
423 Q-15.13
424 Q-15.14
425 Q-15.15
426 Q-15.16
427 Q-15.17
428 Q-15.18
429 Q-15.19
430 Q-15.20
431 Q-15.21
432 Q-15.22
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No. Q
433 Q-15.23
434 Q-15.24
435 Q-15.25
436 Q-15.26
437 Q-15.27
438 Q-15.28
439 Q-15.29
440 Q-15.30
441 Q-16.1
442 Q-16.2
443 Q-16.3
444 Q-16.4
445 Q-16.5
446 Q-16.6
447 Q-16.7
448 Q-16.8
449 Q-16.9
450 Q-16.10
451 Q-16.11
452 Q-16.12
453 Q-16.13
454 Q-16.14
455 Q-16.15
456 Q-16.16
457 Q-16.17
458 Q-16.18
459 Q-16.19
460 Q-16.20
461 Q-16.21
462 Q-16.22
463 Q-16.23
464 Q-16.24
465 Q-16.25
466 Q-16.26
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No. Q
467 Q-16.27
468 Q-16.28
469 Q-16.29
470 Q-16.30
471 Q-16.31
472 Q-16.32
473 Q-16.33
474 Q-16.34
475 Q-16.35
476 Q-16.36
477 Q-16.37
478 Q-16.38
479 Q-16.39
480 Q-16.40
481 Q-16.41
482 Q-16.42
483 Q-16.43
484 Q-16.44
485 Q-16.45
486 Q-16.46
487 Q-16.47
488 Q-16.48
489 Q-16.49
490 Q-16.50
491 Q-16.51
492 Q-16.52
493 Q-16.35
494 Q-16.45
495 Q-16.55
496 Q-16.56
497 Q-16.57
498 Q-16.58
499 Q-16.59
500 Q-16.60
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No. Q
501 Q-16.61
502 Q-16.62
503 Q-16.63
504 Q-16.64
505 Q-16.65
506 Q-16.66
507 Q-16.67
508 Q-16.68
509 Q-16.69
510 Q-16.70
511 Q-16.71
512 Q-16.72
513 Q-16.73
514 Q-16.74
515 Q-16.75
516 Q-16.76
517 Q-16.77
518 Q-16.78
519 Q-16.79
520 Q-16.80
521 Q-17.1
522 Q-17.2
523 Q-17.3
524 Q-17.4
525 Q-17.5
526 Q-17.6
527 Q-17.7
528 Q-17.8
529 Q-17.9
530 Q-17.10
531 Q-18.1
532 Q-18.2
533 Q-18.3
534 Q-18.4
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No. Q
535 Q-18.5
536 Q-18.6
537 Q-18.7
538 Q-18.8
539 Q-18.9
540 Q-18.10
541 Q-19.1
542 Q-19.2
543 Q-19.3
544 Q-19.4
545 Q-19.5
546 Q-19.6
547 Q-19.7
548 Q-19.8
549 Q-19.9
550 Q-19.10
551 Q-19.11
552 Q-19.12
553 Q-19.13
554 Q-19.14
555 Q-19.15
556 Q-23.1
557 Q-23.2
558 Q-23.3
559 Q-23.4
560 Q-23.5
561 Q-23.6
562 Q-23.7
563 Q-23.8
564 Q-23.9
565 Q-23.10
566 Q-23.11
567 Q-23.12
568 Q-23.13
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No. Q
569 Q-23.14
570 Q-23.15
571 Q-23.16
572 Q-23.17
573 Q-23.18
574 Q-23.19
575 Q-23.20
576 Q-23.21
577 Q-23.22
578 Q-23.23
579 Q-23.24
580 Q-23.25
581 Q-23.26
582 Q-23.27
583 Q-23.28
584 Q-23.29
585 Q-23.30
586 Q-23.31
587 Q-23.32
588 Q-23.33
589 Q-23.34
590 Q-23.35
591 Q-23.36
592 Q-23.37
593 Q-23.38
594 Q-23.39
595 Q-23.40
596 Q-23.41
597 Q-23.42
598 Q-23.43
599 Q-23.44
600 Q-23.45
601 Q-23.46
602 Q-23.47
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No. Q
603 Q-23.48
604 Q-23.49
605 Q-23.50
606 Q-23.51
607 Q-23.52
608 Q-23.53
609 Q-23.54
610 Q-23.55
611 Q-23.56
612 Q-23.57
613 Q-23.58
634 Q-25.1
635 Q-25.2
636 Q-25.3
637 Q-25.4
638 Q-25.5
639 Q-25.6
640 Q-25.7
641 Q-25.8
642 Q-25.9
643 Q-25.10
644 Q-25.11
645 Q-25.12
646 Q-25.13
647 Q-25.14
648 Q-25.15
649 Q-25.16
650 Q-25.17
651 Q-25.18
652 Q-25.19
653 Q-25.20
654 Q-25.21
655 Q-25.22
656 Q-25.23
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No. Q
657 Q-25.24
658 Q-25.25
659 Q-25.26
660 Q-25.27
661 Q-25.28
662 Q-25.29
663 Q-25.30
664 Q-25.31
665 Q-25.32
666 Q-25.33
667 Q-25.34
668 Q-25.35
669 Q-25.36
670 Q-25.37
671 Q-25.38
672 Q-25.39
673 Q-25.40
674 Q-25.41
675 Q-25.42
676 Q-25.43
677 Q-25.44
678 Q-25.45
679 Q-26.1
680 Q-26.2
681 Q-26.3
682 Q-26.4
683 Q-26.5
684 Q-26.6
685 Q-26.7
686 Q-26.8
687 Q-26.9
688 Q-26.10
689 Q-26.11
690 Q-26.12
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No. Q
691 Q-26.13
692 Q-26.14
693 Q-26.15
694 Q-12.26
695 Q-12.27
696 Q-12.28
697 Q-12.29
698 Q-12.30
699 Q-27.1
700 Q-27.2
701 Q-27.3
702 Q-27.4
703 Q-27.5
704 Q-28.1
705 Q-28.2
706 Q-28.3
707 Q-28.4
708 Q-28.5
Figure AU2017379281A1_D0091
Table 1.2: Preferred compounds of the formula (1.2) are the compounds 1.2-1 to 1.2-708 in which Q has the meanings of Table 1 indicated in the respective row. Thus, the compounds 1.2-1 to 1.2-708 of Table
1.2 are defined by the meaning of the respective entries Nos. 1 to 708 for Q of Table 1 above.
Figure AU2017379281A1_D0092
Ή
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Table 1.3: Preferred compounds of the formula (1.3) are the compounds 1.3-1 to 1.3-708 in which Q has the meanings of Table 1 indicated in the respective row. Thus, the compounds 1.3-1 to 1.3-708 of Table
1.3 are defined by the meaning of the respective entries Nos. 1 to 708 for Q of Table 1.
Figure AU2017379281A1_D0093
(1.4)
Table 1.4: Preferred compounds of the formula (1.4) are the compounds 1.4-1 to 1.4-708 in which Q has the meanings of Table 1 indicated in the respective row. Thus, the compounds 1.4-1 to 1.4-708 of Table 1.4 are defined by the meaning of the respective entries Nos. 1 to 708 for Q of Table 1 above.
Figure AU2017379281A1_D0094
Table 1.5: Preferred compounds of the formula (1.5) are the compounds 1.5-1 to 1.5-708 in which Q has the meanings of Table 1 indicated in the respective row. Thus, the compounds 1.5-1 to 1.5-708 of Table 1.5 are defined by the meaning of the respective entries Nos. 1 to 708 for Q of Table 1.
Figure AU2017379281A1_D0095
(1.6)
Table 1.6: Preferred compounds of the formula (1.6) are the compounds 1.6-1 to 1.6-708 in which Q has the meanings of Table 1 indicated in the respective row. Thus, the compounds 1.6-1 to 1.6-708 of Table
1.6 are defined by the meaning of the respective entries Nos. 1 to 708 for Q of Table 1 above.
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Figure AU2017379281A1_D0096
o
Table 1.7: Preferred compounds of the formula (1.7) are the compounds 1.7-1 to 1.7-708 in which Q has the meanings of Table 1 indicated in the respective row. Thus, the compounds 1.7-1 to 1.7-708 of Table
1.7 are defined by the meaning of the respective entries Nos. 1 to 708 for Q of Table 1.
Figure AU2017379281A1_D0097
O
Table 1.8: Preferred compounds of the formula (1.8) are the compounds 1.8-1 to 1.8-708 in which Q has the meanings of Table 1 indicated in the respective row. Thus, the compounds 1.8-1 to 1.8-708 of Table
1.8 are defined by the meaning of the respective entries Nos. 1 to 708 for Q of Table 1 above.
Figure AU2017379281A1_D0098
Figure AU2017379281A1_D0099
O
Table 1.9: Preferred compounds of the formula (1.9) are the compounds 1.9-1 to 1.9-708 in which Q has the meanings of Table 1 indicated in the respective row. Thus, the compounds 1.9-1 to 1.9-708 of Table
1.9 are defined by the meaning of the respective entries Nos. 1 to 708 for Q of Table 1.
Figure AU2017379281A1_D0100
Ή
Figure AU2017379281A1_D0101
O
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Table 1.10: Preferred compounds of the formula (1.10) are the compounds 1.10-1 to 1.10-708 in which Q has the meanings of Table 1 indicated in the respective row. Thus, the compounds 1.10-1 to 1.10-708 of
Table 1.10 are defined by the meaning of the respective entries Nos. 1 to 708 for Q of Table 1 above.
Figure AU2017379281A1_D0102
Table 1.11: Preferred compounds of the formula (1.11) are the compounds 1.11-1 to 1.11-708 in which Q has the meanings of Table 1 indicated in the respective row. Thus, the compounds 1.11-1 to 1.11-708 of Table 1.11 are defined by the meaning of the respective entries Nos. 1 to 708 for Q of Table 1.
Figure AU2017379281A1_D0103
(1.12)
Figure AU2017379281A1_D0104
O
Table 1.12: Preferred compounds of the formula (1.12) are the compounds 1.12-1 to 1.12-708 in which Q has the meanings of Table 1 indicated in the respective row. Thus, the compounds 1.12-1 to 1.12-708 of Table 1.12 are defined by the meaning of the respective entries Nos. 1 to 708 for Q of Table 1 above.
Figure AU2017379281A1_D0105
O
Table 1.13: Preferred compounds of the formula (1.13) are the compounds 1.13-1 to 1.13-708 in which Q has the meanings of Table 1 indicated in the respective row. Thus, the compounds 1.13-1 to 1.13-708 of
Table 1.13 are defined by the meaning of the respective entries Nos. 1 to 708 for Q of Table 1.
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Figure AU2017379281A1_D0106
Table 1.14: Preferred compounds of the formula (1.14) are the compounds 1.14-1 to 1.14-708 in which Q has the meanings of Table 1 indicated in the respective row. Thus, the compounds 1.14-1 to 1.14-708 of Table 1.14 are defined by the meaning of the respective entries Nos. 1 to 708 for Q of Table 1 above.
Figure AU2017379281A1_D0107
Table 1.15: Preferred compounds of the formula (1.15) are the compounds 1.15-1 to 1.15-708 in which Q has the meanings of Table 1 indicated in the respective row. Thus, the compounds 1.15-1 to 1.15-708 of Table 1.15 are defined by the meaning of the respective entries Nos. 1 to 708 for Q of Table 1.
Figure AU2017379281A1_D0108
Table 1.16: Preferred compounds of the formula (1.16) are the compounds 1.16-1 to 1.16-708 in which Q has the meanings of Table 1 indicated in the respective row. Thus, the compounds 1.16-1 to 1.16-708 of Table 1.16 are defined by the meaning of the respective entries Nos. 1 to 708 for Q of Table 1 above.
Figure AU2017379281A1_D0109
Ή
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Table 1.17: Preferred compounds of the formula (1.17) are the compounds 1.17-1 to 1.17-708 in which Q has the meanings of Table 1 indicated in the respective row. Thus, the compounds 1.17-1 to 1.17-708 of
Table 1.17 are defined by the meaning of the respective entries Nos. 1 to 708 for Q of Table 1.
Figure AU2017379281A1_D0110
Table 1.18: Preferred compounds of the formula (1.18) are the compounds 1.18-1 to 1.18-708 in which Q has the meanings of Table 1 indicated in the respective row. Thus, the compounds 1.18-1 to 1.18-708 of Table 1.18 are defined by the meaning of the respective entries Nos. 1 to 708 for Q of Table 1 above.
Figure AU2017379281A1_D0111
Table 1.19: Preferred compounds of the formula (1.19) are the compounds 1.19-1 to 1.19-708 in which Q has the meanings of Table 1 indicated in the respective row. Thus, the compounds 1.19-1 to 1.19-708 of Table 1.19 are defined by the meaning of the respective entries Nos. 1 to 708 for Q of Table 1.
Figure AU2017379281A1_D0112
Table 1.20: Preferred compounds of the formula (1.20) are the compounds 1.20-1 to 1.20-708 in which Q has the meanings of Table 1 indicated in the respective row. Thus, the compounds 1.20-1 to 1.20-708 of
Table 1.20 are defined by the meaning of the respective entries Nos. 1 to 708 for Q of Table 1 above.
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Figure AU2017379281A1_D0113
(1-21)
Table 1.21: Preferred compounds of the formula (1.21) are the compounds 1.21-1 to 1.21-708 in which Q has the meanings of Table 1 indicated in the respective row. Thus, the compounds 1.21-1 to 1.21-708 of Table 1.21 are defined by the meaning of the respective entries Nos. 1 to 708 for Q of Table 1.
Figure AU2017379281A1_D0114
Table 1.22: Preferred compounds of the formula (1.22) are the compounds 1.22-1 to 1.22-708 in which Q has the meanings of Table 1 indicated in the respective row. Thus, the compounds 1.22-1 to 1.22-708 of Table 1.22 are defined by the meaning of the respective entries Nos. 1 to 708 for Q of Table 1 above.
Figure AU2017379281A1_D0115
Table 1.23: Preferred compounds of the formula (1.23) are the compounds 1.23-1 to 1.23-708 in which Q has the meanings of Table 1 indicated in the respective row. Thus, the compounds 1.23-1 to 1.23-708 of Table 1.23 are defined by the meaning of the respective entries Nos. 1 to 708 for Q of Table 1.
Figure AU2017379281A1_D0116
Ή
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Table 1.24: Preferred compounds of the formula (1.24) are the compounds 1.24-1 to 1.24-708 in which Q has the meanings of Table 1 indicated in the respective row. Thus, the compounds 1.24-1 to 1.24-708 of
Table 1.24 are defined by the meaning of the respective entries Nos. 1 to 708 for Q of Table 1 above.
Figure AU2017379281A1_D0117
'Ύ0 o
Table 1.25: Preferred compounds of the formula (1.25) are the compounds 1.25-1 to 1.25-708 in which Q has the meanings of Table 1 indicated in the respective row. Thus, the compounds 1.25-1 to 1.25-708 of Table 1.25 are defined by the meaning of the respective entries Nos. 1 to 708 for Q of Table 1.
Figure AU2017379281A1_D0118
'Ύ0 o
Table 1.26: Preferred compounds of the formula (1.26) are the compounds 1.26-1 to 1.26-708 in which Q has the meanings of Table 1 indicated in the respective row. Thus, the compounds 1.26-1 to 1.26-708 of Table 1.26 are defined by the meaning of the respective entries Nos. 1 to 708 for Q of Table 1 above.
Figure AU2017379281A1_D0119
(1-27)
Table 1.27: Preferred compounds of the formula (1.27) are the compounds 1.27-1 to 1.27-708 in which Q has the meanings of Table 1 indicated in the respective row. Thus, the compounds 1.27-1 to 1.27-708 of
Table 1.27 are defined by the meaning of the respective entries Nos. 1 to 708 for Q of Table 1.
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Figure AU2017379281A1_D0120
Ο
Table 1.28: Preferred compounds of the formula (1.28) are the compounds 1.28-1 to 1.28-708 in which Q has the meanings of Table 1 indicated in the respective row. Thus, the compounds 1.28-1 to 1.28-708 of 5 Table 1.28 are defined by the meaning of the respective entries Nos. 1 to 708 for Q of Table 1 above.
Figure AU2017379281A1_D0121
Table 1.29: Preferred compounds of the formula (1.29) are the compounds 1.29-1 to 1.29-708 in which Q has the meanings of Table 1 indicated in the respective row. Thus, the compounds 1.29-1 to 1.29-708 of
Table 1.29 are defined by the meaning of the respective entries Nos. 1 to 708 for Q of Table 1.
Figure AU2017379281A1_D0122
Figure AU2017379281A1_D0123
O
Table 1.30: Preferred compounds of the formula (1.30) are the compounds 1.30-1 to 1.30-708 in which Q has the meanings of Table 1 indicated in the respective row. Thus, the compounds 1.30-1 to 1.30-708 of Table 1.30 are defined by the meaning of the respective entries Nos. 1 to 708 for Q of Table 1 above.
Figure AU2017379281A1_D0124
(1.31)
Ή
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Table 1.31: Preferred compounds of the formula (1.31) are the compounds 1.31-1 to 1.31-708 in which Q has the meanings of Table 1 indicated in the respective row. Thus, the compounds 1.31-1 to 1.31-708 of
Table 1.31 are defined by the meaning of the respective entries Nos. 1 to 708 for Q of Table 1.
Figure AU2017379281A1_D0125
(1.32)
Figure AU2017379281A1_D0126
O
Table 1.32: Preferred compounds of the formula (1.32) are the compounds 1.32-1 to 1.32-708 in which Q has the meanings of Table 1 indicated in the respective row. Thus, the compounds 1.32-1 to 1.32-708 of Table 1.32 are defined by the meaning of the respective entries Nos. 1 to 708 for Q of Table 1 above.
Figure AU2017379281A1_D0127
O
Table 1.33: Preferred compounds of the formula (1.33) are the compounds 1.33-1 to 1.33-708 in which Q has the meanings of Table 1 indicated in the respective row. Thus, the compounds 1.33-1 to 1.33-708 of Table 1.33 are defined by the meaning of the respective entries Nos. 1 to 708 for Q of Table 1.
Figure AU2017379281A1_D0128
O
Table 1.34: Preferred compounds of the formula (1.34) are the compounds 1.34-1 to 1.34-708 in which Q has the meanings of Table 1 indicated in the respective row. Thus, the compounds 1.34-1 to 1.34-708 of
Table 1.34 are defined by the meaning of the respective entries Nos. 1 to 708 for Q of Table 1 above.
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Figure AU2017379281A1_D0129
Table 1.35: Preferred compounds of the formula (1.35) are the compounds 1.35-1 to 1.35-708 in which Q has the meanings of Table 1 indicated in the respective row. Thus, the compounds 1.35-1 to 1.35-708 of 5 Table 1.35 are defined by the meaning of the respective entries Nos. 1 to 708 for Q of Table 1.
Figure AU2017379281A1_D0130
Table 1.36: Preferred compounds of the formula (1.36) are the compounds 1.36-1 to 1.36-708 in which Q has the meanings of Table 1 indicated in the respective row. Thus, the compounds 1.36-1 to 1.36-708 of
Table 1.36 are defined by the meaning of the respective entries Nos. 1 to 708 for Q of Table 1 above.
Figure AU2017379281A1_D0131
Table 1.37: Preferred compounds of the formula (1.37) are the compounds 1.37-1 to 1.37-708 in which Q has the meanings of Table 1 indicated in the respective row. Thus, the compounds 1.37-1 to 1.37-708 of Table 1.37 are defined by the meaning of the respective entries Nos. 1 to 708 for Q of Table 1.
Figure AU2017379281A1_D0132
(1.38)
O
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Table 1.38: Preferred compounds of the formula (1.38) are the compounds 1.38-1 to 1.38-708 in which Q has the meanings of Table 1 indicated in the respective row. Thus, the compounds 1.38-1 to 1.38-708 of
Table 1.38 are defined by the meaning of the respective entries Nos. 1 to 708 for Q of Table 1 above.
Figure AU2017379281A1_D0133
Table 1.39: Preferred compounds of the formula (1.39) are the compounds 1.39-1 to 1.39-708 in which Q has the meanings of Table 1 indicated in the respective row. Thus, the compounds 1.39-1 to 1.39-708 of Table 1.39 are defined by the meaning of the respective entries Nos. 1 to 708 for Q of Table 1.
Figure AU2017379281A1_D0134
Table 1.40: Preferred compounds of the formula (1.40) are the compounds 1.40-1 to 1.40-708 in which Q has the meanings of Table 1 indicated in the respective row. Thus, the compounds 1.40-1 to 1.40-708 of Table 1.40 are defined by the meaning of the respective entries Nos. 1 to 708 for Q of Table 1 above.
Figure AU2017379281A1_D0135
(1-41)
Table 1.41: Preferred compounds of the formula (1.41) are the compounds 1.41-1 to 1.41-708 in which Q has the meanings of Table 1 indicated in the respective row. Thus, the compounds 1.41-1 to 1.41-708 of
Table 1.41 are defined by the meaning of the respective entries Nos. 1 to 708 for Q of Table 1.
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Figure AU2017379281A1_D0136
(1-42)
Table 1.42: Preferred compounds of the formula (1.42) are the compounds 1.42-1 to 1.42-708 in which Q has the meanings of Table 1 indicated in the respective row. Thus, the compounds 1.42-1 to 1.42-708 of Table 1.42 are defined by the meaning of the respective entries Nos. 1 to 708 for Q of Table 1 above.
Figure AU2017379281A1_D0137
Table 1.43: Preferred compounds of the formula (1.43) are the compounds 1.43-1 to 1.43-708 in which Q has the meanings of Table 1 indicated in the respective row. Thus, the compounds 1.43-1 to 1.43-708 of Table 1.43 are defined by the meaning of the respective entries Nos. 1 to 708 for Q of Table 1.
Figure AU2017379281A1_D0138
Table 1.44: Preferred compounds of the formula (1.44) are the compounds 1.44-1 to 1.44-708 in which Q has the meanings of Table 1 indicated in the respective row. Thus, the compounds 1.44-1 to 1.44-708 of Table 1.44 are defined by the meaning of the respective entries Nos. 1 to 708 for Q of Table 1 above.
Figure AU2017379281A1_D0139
Figure AU2017379281A1_D0140
(1.45)
Ή
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Table 1.45: Preferred compounds of the formula (1.45) are the compounds 1.45-1 to 1.45-708 in which Q has the meanings of Table 1 indicated in the respective row. Thus, the compounds 1.45-1 to 1.45-708 of
Table 1.45 are defined by the meaning of the respective entries Nos. 1 to 708 for Q of Table 1.
Figure AU2017379281A1_D0141
Table 1.46: Preferred compounds of the formula (1.46) are the compounds 1.46-1 to 1.46-708 in which Q has the meanings of Table 1 indicated in the respective row. Thus, the compounds 1.46-1 to 1.46-708 of Table 1.46 are defined by the meaning of the respective entries Nos. 1 to 708 for Q of Table 1 above.
Figure AU2017379281A1_D0142
O
Table 1.47: Preferred compounds of the formula (1.47) are the compounds 1.47-1 to 1.47-708 in which Q has the meanings of Table 1 indicated in the respective row. Thus, the compounds 1.47-1 to 1.47-708 of Table 1.47 are defined by the meaning of the respective entries Nos. 1 to 708 for Q of Table 1.
Figure AU2017379281A1_D0143
(1.48)
Table 1.48: Preferred compounds of the formula (1.48) are the compounds 1.48-1 to 1.48-708 in which Q has the meanings of Table 1 indicated in the respective row. Thus, the compounds 1.48-1 to 1.48-708 of
Table 1.48 are defined by the meaning of the respective entries Nos. 1 to 708 for Q of Table 1 above.
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Figure AU2017379281A1_D0144
Table 1.49: Preferred compounds of the formula (1.49) are the compounds 1.49-1 to 1.49-708 in which Q has the meanings of Table 1 indicated in the respective row. Thus, the compounds 1.49-1 to 1.49-708 of 5 Table 1.49 are defined by the meaning of the respective entries Nos. 1 to 708 for Q of Table 1.
Figure AU2017379281A1_D0145
Figure AU2017379281A1_D0146
O
Table 1.50: Preferred compounds of the formula (1.50) are the compounds 1.50-1 to 1.50-708 in which Q has the meanings of Table 1 indicated in the respective row. Thus, the compounds 1.50-1 to 1.50-708 of
Table 1.50 are defined by the meaning of the respective entries Nos. 1 to 708 for Q of Table 1 above.
Figure AU2017379281A1_D0147
(1.51)
Table 1.51: Preferred compounds of the formula (1.51) are the compounds 1.51-1 to 1.51-708 in which Q has the meanings of Table 1 indicated in the respective row. Thus, the compounds 1.51-1 to 1.51-708 of Table 1.51 are defined by the meaning of the respective entries Nos. 1 to 708 for Q of Table 1.
Figure AU2017379281A1_D0148
(1-52)
Ή
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Table 1.52: Preferred compounds of the formula (1.52) are the compounds 1.52-1 to 1.52-708 in which Q has the meanings of Table 1 indicated in the respective row. Thus, the compounds 1.52-1 to 1.52-708 of
Table 1.52 are defined by the meaning of the respective entries Nos. 1 to 708 for Q of Table 1 above.
Figure AU2017379281A1_D0149
O
Table 1.53: Preferred compounds of the formula (1.53) are the compounds 1.53-1 to 1.53-708 in which Q has the meanings of Table 1 indicated in the respective row. Thus, the compounds 1.53-1 to 1.53-708 of Table 1.53 are defined by the meaning of the respective entries Nos. 1 to 708 for Q of Table 1.
Figure AU2017379281A1_D0150
O
Table 1.54: Preferred compounds of the formula (1.54) are the compounds 1.54-1 to 1.54-708 in which Q has the meanings of Table 1 indicated in the respective row. Thus, the compounds 1.54-1 to 1.54-708 of Table 1.54 are defined by the meaning of the respective entries Nos. 1 to 708 for Q of Table 1 above.
Figure AU2017379281A1_D0151
Table 1.55: Preferred compounds of the formula (1.55) are the compounds 1.55-1 to 1.55-708 in which Q has the meanings of Table 1 indicated in the respective row. Thus, the compounds 1.55-1 to 1.55-708 of
Table 1.55 are defined by the meaning of the respective entries Nos. 1 to 708 for Q of Table 1.
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Figure AU2017379281A1_D0152
Table 1.56: Preferred compounds of the formula (1.56) are the compounds 1.56-1 to 1.56-708 in which Q has the meanings of Table 1 indicated in the respective row. Thus, the compounds 1.56-1 to 1.56-708 of 5 Table 1.56 are defined by the meaning of the respective entries Nos. 1 to 708 for Q of Table 1 above.
Figure AU2017379281A1_D0153
Table 1.57: Preferred compounds of the formula (1.57) are the compounds 1.57-1 to 1.57-708 in which Q has the meanings of Table 1 indicated in the respective row. Thus, the compounds 1.57-1 to 1.57-708 of
Table 1.57 are defined by the meaning of the respective entries Nos. 1 to 708 for Q of Table 1.
Figure AU2017379281A1_D0154
Table 1.58: Preferred compounds of the formula (1.58) are the compounds 1.58-1 to 1.58-708 in which Q has the meanings of Table 1 indicated in the respective row. Thus, the compounds 1.58-1 to 1.58-708 of Table 1.58 are defined by the meaning of the respective entries Nos. 1 to 708 for Q of Table 1 above.
Figure AU2017379281A1_D0155
Figure AU2017379281A1_D0156
(1.59)
Ή
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Table 1.59: Preferred compounds of the formula (1.59) are the compounds 1.59-1 to 1.59-708 in which Q has the meanings of Table 1 indicated in the respective row. Thus, the compounds 1.59-1 to 1.59-708 of
Table 1.59 are defined by the meaning of the respective entries Nos. 1 to 708 for Q of Table 1.
Figure AU2017379281A1_D0157
Table 1.60: Preferred compounds of the formula (1.60) are the compounds 1.60-1 to 1.60-708 in which Q has the meanings of Table 1 indicated in the respective row. Thus, the compounds 1.60-1 to 1.60-708 of Table 1.60 are defined by the meaning of the respective entries Nos. 1 to 708 for Q of Table 1 above.
Figure AU2017379281A1_D0158
(1-61)
Table 1.61: Preferred compounds of the formula (1.61) are the compounds 1.61-1 to 1.61-708 in which Q has the meanings of Table 1 indicated in the respective row. Thus, the compounds 1.61-1 to 1.61-708 of Table 1.61 are defined by the meaning of the respective entries Nos. 1 to 708 for Q of Table 1.
Figure AU2017379281A1_D0159
Table 1.62: Preferred compounds of the formula (1.62) are the compounds 1.62-1 to 1.62-708 in which Q has the meanings of Table 1 indicated in the respective row. Thus, the compounds 1.62-1 to 1.62-708 of
Table 1.62 are defined by the meaning of the respective entries Nos. 1 to 708 for Q of Table 1 above.
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Figure AU2017379281A1_D0160
Table 1.63: Preferred compounds of the formula (1.63) are the compounds 1.63-1 to 1.63-708 in which Q has the meanings of Table 1 indicated in the respective row. Thus, the compounds 1.63-1 to 1.63-708 of Table 1.63 are defined by the meaning of the respective entries Nos. 1 to 708 for Q of Table 1.
Figure AU2017379281A1_D0161
Table 1.64: Preferred compounds of the formula (1.64) are the compounds 1.64-1 to 1.64-708 in which Q has the meanings of Table 1 indicated in the respective row. Thus, the compounds 1.64-1 to 1.64-708 of Table 1.64 are defined by the meaning of the respective entries Nos. 1 to 708 for Q of Table 1 above.
Figure AU2017379281A1_D0162
'Ύ0 o
Table 1.65: Preferred compounds of the formula (1.65) are the compounds 1.65-1 to 1.65-708 in which Q has the meanings of Table 1 indicated in the respective row. Thus, the compounds 1.65-1 to 1.65-708 of Table 1.65 are defined by the meaning of the respective entries Nos. 1 to 708 for Q of Table 1.
Figure AU2017379281A1_D0163
'Ύ0 o
Ή
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Table 1.66: Preferred compounds of the formula (1.66) are the compounds 1.66-1 to 1.66-708 in which Q has the meanings of Table 1 indicated in the respective row. Thus, the compounds 1.66-1 to 1.66-708 of
Table 1.66 are defined by the meaning of the respective entries Nos. 1 to 708 for Q of Table 1 above.
Figure AU2017379281A1_D0164
O
Table 1.67: Preferred compounds of the formula (1.67) are the compounds 1.67-1 to 1.67-708 in which Q has the meanings of Table 1 indicated in the respective row. Thus, the compounds 1.67-1 to 1.67-708 of Table 1.67 are defined by the meaning of the respective entries Nos. 1 to 708 for Q of Table 1.
Figure AU2017379281A1_D0165
O
Table 1.68: Preferred compounds of the formula (1.68) are the compounds 1.68-1 to 1.68-708 in which Q has the meanings of Table 1 indicated in the respective row. Thus, the compounds 1.68-1 to 1.68-708 of Table 1.68 are defined by the meaning of the respective entries Nos. 1 to 708 for Q of Table 1 above.
Figure AU2017379281A1_D0166
Table 1.69: Preferred compounds of the formula (1.69) are the compounds 1.69-1 to 1.69-708 in which Q has the meanings of Table 1 indicated in the respective row. Thus, the compounds 1.69-1 to 1.69-708 of
Table 1.69 are defined by the meaning of the respective entries Nos. 1 to 708 for Q of Table 1.
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Figure AU2017379281A1_D0167
Table 1.70: Preferred compounds of the formula (1.70) are the compounds 1.70-1 to 1.70-708 in which Q has the meanings of Table 1 indicated in the respective row. Thus, the compounds 1.70-1 to 1.70-708 of Table 1.70 are defined by the meaning of the respective entries Nos. 1 to 708 for Q of Table 1 above.
Figure AU2017379281A1_D0168
Figure AU2017379281A1_D0169
O
Table 1.71: Preferred compounds of the formula (1.71) are the compounds 1.71-1 to 1.71-708 in which Q has the meanings of Table 1 indicated in the respective row. Thus, the compounds 1.71-1 to 1.71-708 of Table 1.71 are defined by the meaning of the respective entries Nos. 1 to 708 for Q of Table 1.
Figure AU2017379281A1_D0170
(1-72)
Table 1.72: Preferred compounds of the formula (1.72) are the compounds 1.72-1 to 1.72-708 in which Q has the meanings of Table 1 indicated in the respective row. Thus, the compounds 1.72-1 to 1.72-708 of Table 1.72 are defined by the meaning of the respective entries Nos. 1 to 708 for Q of Table 1 above.
Figure AU2017379281A1_D0171
O
Ή
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Table 1.73: Preferred compounds of the formula (1.73) are the compounds 1.73-1 to 1.73-708 in which Q has the meanings of Table 1 indicated in the respective row. Thus, the compounds 1.73-1 to 1.73-708 of
Table 1.73 are defined by the meaning of the respective entries Nos. 1 to 708 for Q of Table 1.
Figure AU2017379281A1_D0172
O
Table 1.74: Preferred compounds of the formula (1.74) are the compounds 1.74-1 to 1.74-708 in which Q has the meanings of Table 1 indicated in the respective row. Thus, the compounds 1.74-1 to 1.74-708 of Table 1.74 are defined by the meaning of the respective entries Nos. 1 to 708 for Q of Table 1 above.
Figure AU2017379281A1_D0173
O
Table 1.75: Preferred compounds of the formula (1.75) are the compounds 1.75-1 to 1.75-708 in which Q has the meanings of Table 1 indicated in the respective row. Thus, the compounds 1.75-1 to 1.75-708 of Table 1.75 are defined by the meaning of the respective entries Nos. 1 to 708 for Q of Table 1.
(ΤΝΖ (1.76) ^Y°H
Table 1.76: Preferred compounds of the formula (1.76) are the compounds 1.76-1 to 1.76-708 in which Q has the meanings of Table 1 indicated in the respective row. Thus, the compounds 1.76-1 to 1.76-708 of
Table 1.76 are defined by the meaning of the respective entries Nos. 1 to 708 for Q of Table 1 above.
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Figure AU2017379281A1_D0174
Table 1.77: Preferred compounds of the formula (1.77) are the compounds 1.77-1 to 1.77-708 in which Q has the meanings of Table 1 indicated in the respective row. Thus, the compounds 1.77-1 to 1.77-708 of Table 1.77 are defined by the meaning of the respective entries Nos. 1 to 708 for Q of Table 1 above.
Figure AU2017379281A1_D0175
Table 1.78: Preferred compounds of the formula (1.78) are the compounds 1.78-1 to 1.78-708 in which Q has the meanings of Table 1 indicated in the respective row. Thus, the compounds 1.78-1 to 1.78-708 of Table 1.78 are defined by the meaning of the respective entries Nos. 1 to 708 for Q of Table 1 above.
Figure AU2017379281A1_D0176
Table 1.79: Preferred compounds of the formula (1.79) are the compounds 1.79-1 to 1.79-708 in which Q has the meanings of Table 1 indicated in the respective row. Thus, the compounds 1.79-1 to 1.79-708 of Table 1.79 are defined by the meaning of the respective entries Nos. 1 to 708 for Q of Table 1 above.
Figure AU2017379281A1_D0177
Ή
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Table 1.80: Preferred compounds of the formula (1.80) are the compounds 1.80-1 to 1.80-708 in which Q has the meanings of Table 1 indicated in the respective row. Thus, the compounds 1.80-1 to 1.80-708 of
Table 1.80 are defined by the meaning of the respective entries Nos. 1 to 708 for Q of Table 1 above.
Figure AU2017379281A1_D0178
Table 1.81: Preferred compounds of the formula (1.81) are the compounds 1.81-1 to 1.81-708 in which Q has the meanings of Table 1 indicated in the respective row. Thus, the compounds 1.81-1 to 1.81-708 of Table 1.81 are defined by the meaning of the respective entries Nos. 1 to 708 for Q of Table 1.
Figure AU2017379281A1_D0179
Table 1.82: Preferred compounds of the formula (1.82) are the compounds 1.82-1 to 1.82-708 in which Q has the meanings of Table 1 indicated in the respective row. Thus, the compounds 1.82-1 to 1.82-708 of Table 1.82 are defined by the meaning of the respective entries Nos. 1 to 708 for Q of Table 1 above.
Figure AU2017379281A1_D0180
Table 1.83: Preferred compounds of the formula (1.83) are the compounds 1.83-1 to 1.83-708 in which Q has the meanings of Table 1 indicated in the respective row. Thus, the compounds 1.83-1 to 1.83-708 of
Table 1.83 are defined by the meaning of the respective entries Nos. 1 to 708 for Q of Table 1.
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Figure AU2017379281A1_D0181
Table 1.84: Preferred compounds of the formula (1.84) are the compounds 1.84-1 to 1.84-708 in which Q has the meanings of Table 1 indicated in the respective row. Thus, the compounds 1.84-1 to 1.84-708 of 5 Table 1.84 are defined by the meaning of the respective entries Nos. 1 to 708 for Q of Table 1 above.
Figure AU2017379281A1_D0182
(1.85)
Table 1.85: Preferred compounds of the formula (1.85) are the compounds 1.85-1 to 1.85-708 in which Q has the meanings of Table 1 indicated in the respective row. Thus, the compounds 1.85-1 to 1.85-708 of
Table 1.85 are defined by the meaning of the respective entries Nos. 1 to 708 for Q of Table 1.
Figure AU2017379281A1_D0183
Table 1.86: Preferred compounds of the formula (1.86) are the compounds 1.86-1 to 1.86-708 in which Q has the meanings of Table 1 indicated in the respective row. Thus, the compounds 1.86-1 to 1.86-708 of
Table 1.86 are defined by the meaning of the respective entries Nos. 1 to 708 for Q of Table 1 above.
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Figure AU2017379281A1_D0184
(1.87)
Table 1.87: Preferred compounds of the formula (1.87) are the compounds 1.87-1 to 1.87-708 in which Q has the meanings of Table 1 indicated in the respective row. Thus, the compounds 1.87-1 to 1.87-708 of 5 Table 1.87 are defined by the meaning of the respective entries Nos. 1 to 708 for Q of Table 1.
Figure AU2017379281A1_D0185
Figure AU2017379281A1_D0186
O
Table 1.88: Preferred compounds of the formula (1.88) are the compounds 1.88-1 to 1.88-708 in which Q has the meanings of Table 1 indicated in the respective row. Thus, the compounds 1.88-1 to 1.88-708 of
Table 1.88 are defined by the meaning of the respective entries Nos. 1 to 708 for Q of Table 1 above.
O
Figure AU2017379281A1_D0187
O (1.89)
Table 1.89: Preferred compounds of the formula (1.89) are the compounds 1.89-1 to 1.89-708 in which Q has the meanings of Table 1 indicated in the respective row. Thus, the compounds 1.89-1 to 1.89-708 of
Table 1.89 are defined by the meaning of the respective entries Nos. 1 to 708 for Q of Table 1.
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Figure AU2017379281A1_D0188
(1.90)
Table 1.90: Preferred compounds of the formula (1.90) are the compounds 1.90-1 to 1.90-708 in which Q has the meanings of Table 1 indicated in the respective row. Thus, the compounds 1.90-1 to 1.90-708 of Table 1.90 are defined by the meaning of the respective entries Nos. 1 to 708 for Q of Table 1 above.
Figure AU2017379281A1_D0189
Table 1.91: Preferred compounds of the formula (1.91) are the compounds 1.91-1 to 1.91-708 in which Q has the meanings of Table 1 indicated in the respective row. Thus, the compounds 1.91-1 to 1.91-708 of Table 1.91 are defined by the meaning of the respective entries Nos. 1 to 708 for Q of Table 1.
Figure AU2017379281A1_D0190
Table 1.92: Preferred compounds of the formula (1.92) are the compounds 1.92-1 to 1.92-708 in which Q has the meanings of Table 1 indicated in the respective row. Thus, the compounds 1.92-1 to 1.92-708 of Table 1.92 are defined by the meaning of the respective entries Nos. 1 to 708 for Q of Table 1 above.
Figure AU2017379281A1_D0191
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Table 1.93: Preferred compounds of the formula (1.93) are the compounds 1.93-1 to 1.93-708 in which Q has the meanings of Table 1 indicated in the respective row. Thus, the compounds 1.93-1 to 1.93-708 of Table 1.93 are defined by the meaning of the respective entries Nos. 1 to 708 for Q of Table 1.
Figure AU2017379281A1_D0192
Table 1.94: Preferred compounds of the formula (1.94) are the compounds 1.94-1 to 1.94-708 in which Q has the meanings of Table 1 indicated in the respective row. Thus, the compounds 1.94-1 to 1.94-708 of Table 1.94 are defined by the meaning of the respective entries Nos. 1 to 708 for Q of Table 1 above.
Figure AU2017379281A1_D0193
Table 1.95: Preferred compounds of the formula (1.95) are the compounds 1.95-1 to 1.95-708 in which Q has the meanings of Table 1 indicated in the respective row. Thus, the compounds 1.95-1 to 1.95-708 of Table 1.95 are defined by the meaning of the respective entries Nos. 1 to 708 for Q of Table 1.
Figure AU2017379281A1_D0194
Table 1.96: Preferred compounds of the formula (1.96) are the compounds 1.96-1 to 1.96-708 in which Q has the meanings of Table 1 indicated in the respective row. Thus, the compounds 1.96-1 to 1.96-708 of
Table 1.96 are defined by the meaning of the respective entries Nos. 1 to 708 for Q of Table 1 above.
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Figure AU2017379281A1_D0195
(1.97)
Table 1.97: Preferred compounds of the formula (1.97) are the compounds 1.97-1 to 1.97-708 in which Q has the meanings of Table 1 indicated in the respective row. Thus, the compounds 1.97-1 to 1.97-708 of Table 1.97 are defined by the meaning of the respective entries Nos. 1 to 708 for Q of Table 1.
Figure AU2017379281A1_D0196
Table 1.98: Preferred compounds of the formula (1.98) are the compounds 1.98-1 to 1.98-708 in which Q has the meanings of Table 1 indicated in the respective row. Thus, the compounds 1.98-1 to 1.98-708 of Table 1.98 are defined by the meaning of the respective entries Nos. 1 to 708 for Q of Table 1 above.
Figure AU2017379281A1_D0197
Table 1.99: Preferred compounds of the formula (1.99) are the compounds 1.99-1 to 1.99-708 in which Q has the meanings of Table 1 indicated in the respective row. Thus, the compounds 1.99-1 to 1.99-708 of Table 1.99 are defined by the meaning of the respective entries Nos. 1 to 708 for Q of Table 1.
Figure AU2017379281A1_D0198
(1.100)
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Table 1.100: Preferred compounds of the formula (1.100) are the compounds 1.100-1 to 1.100-708 in which Q has the meanings of Table 1 indicated in the respective row. Thus, the compounds 1.100-1 to 1.100-708 of Table 1.100 are defined by the meaning of the respective entries Nos. 1 to 708 for Q of
Table 1 above. K q n>cci (M01) ύ°η 0
Table 1.101: Preferred compounds of the formula (1.101) are the compounds 1.101-1 to 1.101-708 in which Q has the meanings of Table 1 indicated in the respective row. Thus, the compounds 1.101 -1 to 1.101-708 of Table 1.101 are defined by the meaning of the respective entries Nos. 1 to 708 for Q of Table 1.
Figure AU2017379281A1_D0199
(1.102)
Table 1.102: Preferred compounds of the formula (1.102) are the compounds 1.102-1 to 1.102-708 in which Q has the meanings of Table 1 indicated in the respective row. Thus, the compounds 1.102-1 to
1.102-708 of Table 1.102 are defined by the meaning of the respective entries Nos. 1 to 708 for Q of Table 1 above.
Figure AU2017379281A1_D0200
Table 1.103: Preferred compounds of the formula (1.103) are the compounds 1.103-1 to 1.103-708 in which Q has the meanings of Table 1 indicated in the respective row. Thus, the compounds 1.103-1 to
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1.103-708 of Table 1.103 are defined by the meaning of the respective entries Nos. 1 to 708 for Q of Table 1.
Figure AU2017379281A1_D0201
Table 1.104: Preferred compounds of the formula (1.104) are the compounds 1.104-1 to 1.104-708 in which Q has the meanings of Table 1 indicated in the respective row. Thus, the compounds 1.104-1 to
1.104-708 of Table 1.104 are defined by the meaning of the respective entries Nos. 1 to 708 for Q of Table 1 above.
Figure AU2017379281A1_D0202
Table 1.105: Preferred compounds of the formula (1.105) are the compounds 1.105-1 to 1.105-708 in which Q has the meanings of Table 1 indicated in the respective row. Thus, the compounds 1.105-1 to
1.105-708 of Table 1.105 are defined by the meaning of the respective entries Nos. 1 to 708 for Q of Table 1 above.
Figure AU2017379281A1_D0203
Table 1.106: Preferred compounds of the formula (1.106) are the compounds 1.106-1 to 1.106-708 in which Q has the meanings of Table 1 indicated in the respective row. Thus, the compounds 1.106-1 to
1.106-708 of Table 1.106 are defined by the meaning of the respective entries Nos. 1 to 708 for Q of
Table 1 above.
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Figure AU2017379281A1_D0204
(1.107)
Table 1.107: Preferred compounds of the formula (1.107) are the compounds 1.107-1 to 1.107-708 in which Q has the meanings of Table 1 indicated in the respective row. Thus, the compounds 1.107-1 to 1.107-708 of Table 1.107 are defined by the meaning of the respective entries Nos. 1 to 708 for Q of Table 1 above.
Figure AU2017379281A1_D0205
(1.108)
Table 1.108: Preferred compounds of the formula (1.108) are the compounds 1.108-1 to 1.108-708 in which Q has the meanings of Table 1 indicated in the respective row. Thus, the compounds 1.108-1 to 1.108-708 of Table 1.108 are defined by the meaning of the respective entries Nos. 1 to 708 for Q of Table 1 above.
Figure AU2017379281A1_D0206
Table 1.109: Preferred compounds of the formula (1.109) are the compounds 1.109-1 to 1.109-708 in which Q has the meanings of Table 1 indicated in the respective row. Thus, the compounds 1.109-1 to
1.109-708 of Table 1.109 are defined by the meaning of the respective entries Nos. 1 to 708 for Q of
Table 1 above.
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Figure AU2017379281A1_D0208
110)
Table 1.110: Preferred compounds of the formula (1.110) are the compounds 1.110-1 to 1.110-708 in which Q has the meanings of Table 1 indicated in the respective row. Thus, the compounds 1.110-1 to 1.110-708 of Table 1.110 are defined by the meaning of the respective entries Nos. 1 to 708 for Q of Table 1 above.
Figure AU2017379281A1_D0209
Table 1.111: Preferred compounds of the formula (1.111) are the compounds 1.111-1 to 1.111-708 in which Q has the meanings of Table 1 indicated in the respective row. Thus, the compounds 1.111 -1 to 1.111-708 of Table 1.111 are defined by the meaning of the respective entries Nos. 1 to 708 for Q of Table 1 above.
Figure AU2017379281A1_D0210
Table 1.112: Preferred compounds of the formula (1.112) are the compounds 1.112-1 to 1.112-708 in which Q has the meanings of Table 1 indicated in the respective row. Thus, the compounds 1.112-1 to
1.112-708 of Table 1.112 are defined by the meaning of the respective entries Nos. 1 to 708 for Q of
Table 1 above.
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Figure AU2017379281A1_D0211
Table 1.113: Preferred compounds of the formula (1.113) are the compounds 1.113-1 to 1.113-708 in which Q has the meanings of Table 1 indicated in the respective row. Thus, the compounds 1.113 -1 to 1.113-708 of Table 1.113 are defined by the meaning of the respective entries Nos. 1 to 708 for Q of Table 1 above.
Figure AU2017379281A1_D0212
Table 1.114: Preferred compounds of the formula (1.114) are the compounds 1.114-1 to 1.114-708 in which Q has the meanings of Table 1 indicated in the respective row. Thus, the compounds 1.114-1 to 1.114-708 of Table 1.114 are defined by the meaning of the respective entries Nos. 1 to 708 for Q of Table 1 above.
Figure AU2017379281A1_D0213
Table 1.115: Preferred compounds of the formula (1.115) are the compounds 1.115-1 to 1.115-708 in which Q has the meanings of Table 1 indicated in the respective row. Thus, the compounds 1.115-1 to
1.115-708 of Table 1.115 are defined by the meaning of the respective entries Nos. 1 to 708 for Q of
Table 1 above.
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Figure AU2017379281A1_D0214
Figure AU2017379281A1_D0215
Ο
Table 1.116: Preferred compounds of the formula (1.116) are the compounds 1.116-1 to 1.116-708 in which Q has the meanings of Table 1 indicated in the respective row. Thus, the compounds 1.116-1 to 1.116-708 of Table 1.116 are defined by the meaning of the respective entries Nos. 1 to 708 for Q of Table 1 above.
Spectroscopic data of selected table examples:
The spectroscopic data listed hereinafter for selected table examples were evaluated via conventional Ή NMR interpretation or via NMR peak list methods.
a) Conventional Ή NMR interpretation
Example No. 1.1-287:
'H-NMR (400 MHz, de-DMSO δ, ppm) 7.14 (br. d, 1H), 6.11 (s, 1H), 6.03 (m, 1H), 5.90 (br. d, 1H), 2.21 (s, 3H), 2.04 (s, 3H).
Example No. 1.1-288:
'H-NMR (400 MHz, CDC13 δ, ppm) 6.31 (s, 1H), 6.18 (br. d, 1H), 6.03 (br. d, 1H), 5.95 (s, 1H), 2.69 (q, 2H), 2.16 (s, 3H), 1.30 (t, 3H).
Example No. 1.1-289:
'H-NMR (400 MHz, de-DMSO δ, ppm) 7.13 (br. d, 1H), 6.21 (s, 1H), 6.04 (m, 1H), 5.91 (br. d, 1H), 3.00-2.92 (sept, 1H), 2.04 (s, 3H), 1.23 (d, 6H).
Example No. 1.1-449:
'H-NMR (400 MHz, CDC13 δ, ppm) 8.66 (s, 1H), 8.45 (d, 1H), 7.24 (m, 1H), 6.09 (d, 1H), 5.96 (s, 1H),
5.27 (br. d, 1H), 2.18 (s, 3H).
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Example No. 1.1-697:
'H-NMR (400 MHz, CDC13 δ, ppm) 6.28 (s, 1H), 6.15 (br. d, 1H), 6.03 (br. d, 1H), 5.95 (s, 1H), 2.582.49 (m, 2H), 2.17 (s, 3H), 2.07-1.99 (m, 1H), 0.98 (d, 6H).
Example No. 1.2-162:
'H-NMR (400 MHz, CDC13 δ, ppm) 6.92 (m, 1H), 6.22 (m, 1H), 5.65 (s, 1H), 4.72 (br. d, 1H), 1.99 (s, 3H), 1.31 (s, 9H).
Example No. 1.2-290:
'H-NMR (400 MHz, de-DMSO δ, ppm) 6.97 (m, 1H), 6.90 (d, 1H), 6.25 (s, 1H), 6.00 (m, 1H), 1.85 (s, 3H), 1.27 (s, 9H).
Example No. 1.3-162:
'H-NMR (400 MHz, CDC13 δ, ppm) 7.11 (s, 1H), 6.70 (s, 1H), 6.00 (m, 1H), 2.19 (s, 3H), 1.34 (s, 9H).
Example No. 1.3-287:
'H-NMR (400 MHz, CDC13 δ, ppm) 7.14 (s, 1H), 6.22 (s, 1H), 6.03 (m, 1H), 2.27 (s, 3H), 2.18 (s, 3H), 2.07 (s, 3H).
Example No. 1.3-289:
'H-NMR (400 MHz, CDC13 δ, ppm) 7.14 (s, 1H), 6.26 (s, 1H), 6.03 (m, 1H), 3.08-2.98 (sept, 1H), 2.19 (s, 3H), 2.07 (s, 3H), 1.30 (d, 6H).
Example No. 1.3-290:
'H-NMR (400 MHz, CDC13 δ, ppm) 7.14 (s, 1H), 6.40 (s, 1H), 6.03 (m, 1H), 2.20 (s, 3H), 2.07 (s, 3H), 1.33 (s, 9H).
Example No. 1.5-162:
'H-NMR (400 MHz, CDC13 δ, ppm) 7.13 (s, 1H), 6.70 (s, 1H), 6.00 (m, 1H), 2.55-2.40 (m, 2H), 2.06 (s, 3H), 1.34 (s, 9H), 1.20 (t, 3H).
Example No. 1.5-287:
'H-NMR (400 MHz, CDC13 δ, ppm) 7.16 (s, 1H), 6.22 (s, 1H), 6.02 (m, 1H), 2.53-2.38 (m, 2H), 2.27 (s,
3H), 2.07 (s, 3H), 1.19 (t, 3H).
Example No. 1.5-290:
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Ή-NMR (400 MHz, CDC13 δ, ppm) 7.15 (s, 1H), 6.29 (s, 1H), 6.03 (m, 1H), 2.57-2.39 (m, 2H), 2.06 (s, 3H), 1.33 (s, 9H), 1.20 (t, 3H).
Example No. 1.5-449:
'H-NMR (400 MHz, CDC13 δ, ppm) 8.72 (m, 1H), 7.57 (m, 1H), 7.53 (m, 1H), 7.32 (s, 1H), 5.72 (m, 1H), 2.28-2.22 (m, 1H), 2.11 (s, 3H), 2.10-2.00 (m, 1H).
Example No. 1.6-290:
'H-NMR (400 MHz, CDC13 δ, ppm) 7.01 (m, 1H), 6.92 (m, 1H), 6.34 (s, 1H), 2.52-2.35 (m, 2H), 2.00 (m, 3H), 1.34 (s, 9H), 1.18 (t, 3H).
Example No. 1.11-287:
'H-NMR (400 MHz, CDC13 δ, ppm) 6.96 (s, 1H), 6.22 (s, 1H), 6.03 (m, 1H), 4.38-4.30 (m, 2H), 2.28 (s, 3H),2.12(s, 3H), 1.36 (t, 3H).
Example No. 1.11-290:
'H-NMR (400 MHz, CDC13 δ, ppm) 6.96 (s, 1H), 6.29 (s, 1H), 6.03 (m, 1H), 4.34 (q, 2H), 2.12 (s, 3H), 1.37 (t, 3H), 1.33 (s, 9H).
Example No. 1.21-162:
'H-NMR (400 MHz, CDC13 δ, ppm) 6.72 (s, 1H), 6.13 (br. d, 1H), 5.94 (s, 1H), 4.38 (br. d, 1H), 1.35 (s, 9H), 1.30 (s, 9H).
Example No. 1.25-162:
'H-NMR (400 MHz, CDC13 δ, ppm) 7.38 (s, 1H), 6.70 (s, 1H), 6.01 (s, 1H), 2.52-2.33 (m, 2H), 1.33 (s, 9H), 1.24 (s, 9H), 1.17 (t, 3H).
Example No. 1.31-162:
'H-NMR (400 MHz, CDC13 δ, ppm) 7.18 (s, 1H), 6.69 (s, 1H), 6.01 (s, 1H), 4.38-4.33 (m, 2H), 1.33 (s, 9H), 1.37-1.33 (t, 3H), 1.34 (s, 9H).
Example No. 1.106-162:
'H-NMR (400 MHz, CDC13 δ, ppm) 6.67 (s, 1H), 6.48 (s, 1H), 6.03 (br. d, 1H), 4.57 (br. d, 1H), 1.36 (s,
9H).
Example No. 1.93-162:
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Ή-NMR (400 MHz, CDC13 δ, ppm) 6.69 (s, 1H), 5.95 (br. d, 1H), 5.18 (s, 1H), 4.40 (br. d, 1H), 3.93 (s, 3H), 1.35 (s, 9H).
b) NMR peak list method
The Ή NMR data of selected examples are stated in the form of Ή NMR peak lists. For each signal peak, first the δ value in ppm and then the signal intensity in round brackets are listed. The δ value signal intensity number pairs for different signal peaks are listed with separation from one another by semicolons.
Accordingly, the peak list of an example has the form: δι (intensity?; 62 (intensity?);........; δ;
(intensity?;......; δη (intensityn) The intensity of sharp signals correlates with the height of the signals (in cm) in a printed example of an NMR spectrum and shows the true ratios of the signal intensities. In the case of broad signals, several peaks or the middle of the signal and the relative intensity thereof may be shown in comparison to the most intense signal in the spectrum. For calibration of the chemical shift of ' f f NMR spectra, we use tetramethylsilane and/or the chemical shift of the solvent, particularly in the case of spectra which are measured in DMSO. Therefore, the tetramethylsilane peak may but need not occur in NMR peak lists.
The lists of the 'fl NMR peaks are similar to the conventional 'fl NMR printouts and thus usually contain all peaks listed in a conventional NMR interpretation.
In addition, like conventional 1H NMR printouts, they may show solvent signals, signals of stereoisomers of the target compounds, which likewise form part of the subject-matter of the invention, and/or peaks of impurities. In the reporting of compound signals within the delta range of solvents and/or water, our lists of Ή NMR peaks show the standard solvent peaks, for example peaks of DMSO in DMSO-De and the peak of water, which usually have a high intensity on average. The peaks of stereoisomers of the target compounds and/or peaks of impurities usually have a lower intensity on average than the peaks of the target compounds (for example with a purity of > 90%). Such stereoisomers and/or impurities may be typical of the particular preparation process. Their peaks can thus help in identifying reproduction of our preparation process with reference to by-product fingerprints. An expert calculating the peaks of the target compounds by known methods (MestreC, ACD simulation, but also with empirically evaluated expected values) can, if required, isolate the peaks of the target compounds, optionally using additional intensity filters. This isolation would be similar to the relevant peak picking in conventional 1H NMR interpretation. Further details of 'fl NMR peak lists can be found in the Research Disclosure Database Number 564025.
Example No. 1.5-162: 1H-NMR(400.0 MHz, CDC13):
δ= 7.2614 (6.2); 7.1310 (0.9); 6.6953 (2.1); 2.4798 (0.5); 2.4609 (0.6); 2.4441 (0.6); 2.4254 (0.5); 2.0585 (1.8); 2.0572 (1.8); 2.0545 (1.9); 2.0532 (1.7); 1.3375 (16.0); 1.2168 (1.4); 1.1979 (2.9); 1.1791 (1.3); 0.0002 (2,4)
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Example No. 1.1-162: 1H-NMR(400.0 MHz, CDC13): δ= 7.2614 (4.7); 6.7184 (2.2); 2.1611 (1.7); 2.1597 (1.8); 2.1571 (1.9); 2.1557 (1.8); 1.3567 (16.0); 0.0002(1.7)
Example No. 1.2-449: 1H-NMR(400.0 MHz, CDC13): δ= 8.3621 (2.4); 8.3491 (2.4); 7.2614 (33.2); 7.0104 (2.0); 7.0085 (2.0); 6.9973 (2.1); 6.9954 (2.0); 6.9467 (0.8); 6.9427 (2.9); 6.9386 (4.6); 6.9345 (3.1); 6.9305 (0.8); 6.8535 (0.6); 6.8270 (1.4); 6.8226 (2.0); 6.8178 (3.3); 6.8157 (3.7); 6.8141 (4.2); 6.8052 (0.5); 6.8007 (1.4); 6.7963 (1.9); 6.7919 (1.3); 6.1807 (0.6); 5.2638 (0.7); 5.2380 (0.7); 2.0111 (8.8); 2.0068 (16.0); 2.0024 (8.7); 1.9773 (1.4); 1.9735 (2.3); 1.9696 (1.4); 1.5873 (1.2); -0.0002 (11.5)
Example No. 1.1-449: 1H-NMR(400.0 MHz, CDC13): δ= 8.6599 (4.7); 8.4501 (3.3); 8.4370 (3.4); 7.2610 (27.0); 7.2432 (2.6); 7.2404 (2.6); 7.2306 (2.5); 7.2272 (2.4); 6.0893 (3.7); 6.0808 (3.7); 5.9614 (3.7); 5.9578 (3.6); 5.2747 (5.4); 5.2660 (5.2); 2.1808 (16.0); 2.1769 (15.9); 1.5614 (5.9); -0.0002 (9.4)
Example No. 1.1-451: 1H-NMR(400.0 MHz, CDC13): δ= 8.7554 (8.0); 8.4067 (7.6); 7.2608 (34.4); 6.0731 (3.5); 6.0639 (3.6); 5.9651 (3.6); 5.9612 (3.7); 4.9272 (4.4); 4.9179 (4.3); 2.1805 (15.0); 2.1794 (15.5); 2.1766 (16.0); 2.1755 (15.1); 1.5581 (4.5); - 0.0002 (12.2)
Example No. 1.3-162: 1H-NMR(400.6 MHz, CDC13): δ= 7.2606 (19.6); 7.1139 (1.0); 6.7033 (1.8); 5.9989 (0.6); 5.9950 (0.6); 2.1862 (5.7); 2.0667 (2.3); 2.0631 (2.3); 1.5502 (5.0); 1.3414 (16.0); 1.2619 (1.0); 0.0077 (1.3); -0.0002 (33.5); -0.0083 (1.3)
Example No. 1.11-162: 1H-NMR(400.0 MHz, CDC13): δ= 7.2624 (4.4); 6.9487 (0.7); 6.9475 (0.9); 6.9462 (0.7); 6.6835 (2.2); 5.2989 (0.6); 4.3568 (0.6); 4.3474 (0.6); 4.3389 (0.6); 4.3296 (0.6); 2.1190 (1.7); 2.1176 (1.9); 2.1149 (1.8); 2.1135 (1.7); 1.5628 (0.8); 1.3823 (1.4); 1.3645 (3.0); 1.3466 (1.6); 1.3425 (1.6); 1.3360 (16.0); -0.0002 (1.7)
Example No. 1.5-451: 1H-NMR(400.0 MHz, CDC13): δ= 8.6680 (3.8); 8.6669 (4.7); 8.3887 (4.4); 7.4246 (3.5); 7.4234 (4.4); 7.4220 (3.4); 7.2612 (29.6); 6.0158 (1.0); 6.0128 (2.6); 6.0117 (2.6); 6.0087 (2.7); 6.0077 (2.6); 6.0047 (1.0); 2.3792 (1.1); 2.3739 (1.1); 2.3601 (3.4); 2.3551 (3.5); 2.3411 (3.6); 2.3363 (3.6); 2.3221 (1.3); 2.3176 (1.3); 2.0850 (9.0); 2.0835 (9.5); 2.0809 (9.8); 2.0794 (9.1); 1.5498 (9.4); 1.1738 (7.5); 1.1549 (16.0); 1.1360 (7.0); -0.0002 (11.2)
Example No. 1.5-449: 1H-NMR(400.0 MHz, CDC13): δ= 8.7142 (2.7); 8.7016 (2.7); 7.5644 (2.1); 7.5518 (2.0); 7.5243 (3.8); 7.3226 (2.7); 7.2616 (51.9); 5.7196 (0.8); 5.7158 (2.8); 5.7120 (4.2); 5.7081 (2.9); 5.7044 (0.8); 5.2993 (2.6); 2.2798 (1.6); 2.2613 (1.5); 2.2565 (0.8); 2.2428 (0.6); 2.2379 (2.0); 2.2194 (2.1); 2.2009 (0.7); 2.1630 (1.0); 2.1609 (0.9); 2.1012 (10.4); 2.0994 (11.8); 2.0978 (12.0); 2.0960 (11.1); 2.0812 (0.7); 2.0629 (1.8); 2.0446 (1.9); 2.0395 (0.6); 2.0263 (0.7); 2.0210 (1.3); 2.0026 (1.3); 1.5528 (5.4); 1.5001 (0.7); 1.4823 (0.7); 1.1401 (7.9); 1.1217 (16.0); 1.1033 (7.3); 0.0079 (0.6); -0.0002 (18.2); -0.0083 (0.5)
Example No. 1.3-67: 'H-NMR(599.8 MHz, de-DMSO): δ= 6.9076 (2.8); 6.2424 (1.6); 6.2404 (1.5); 5.7535 (0.8); 5.2114 (0.4); 5.2010 (0.9); 5.1977 (0.4); 5.1906 (1.2); 5.1802 (0.8); 5.1698 (0.3); 3.3239 (50.0); 2.5199 (0.4); 2.5167 (0.4); 2.5078 (6.0); 2.5051 (12.2); 2.5021 (16.6); 2.4991 (12.8); 2.4963 (6.6); 2.0838 (5.4); 2.0819 (5.6); 2.0463 (12.0); 1.3474 (10.5); 1.3401 (3.4); 1.3369 (10.7); 1.3216(0.6); 1.3182 (0.6); 1.3114(0.4); -0.0001 (0.4)
Example No. 1.5-67: 1H-NMR(400.0 MHz, CDC13): δ= 7.2620 (29.0); 6.9919 (3.0); 6.0520 (1.5); 6.0506 (1.6); 6.0479 (1.6); 6.0466 (1.6); 5.2994 (0.6); 5.2837 (1.4); 5.2680 (1.8); 5.2523 (1.3); 2.3877 (1.2); 2.3688 (4.0); 2.3499 (4.4); 2.3310 (1.6); 2.0955 (5.7); 2.0944 (6.1); 2.0916 (6.3); 2.0904 (5.9); 2.0819 (0.8); 2.0802 (0.8); 2.0778 (0.7); 2.0762 (0.6); 1.5566 (3.9); 1.4146 (1.3); 1.4113 (1.4); 1.3987 (2.0); 1.3930 (16.0); 1.3773 (15.6); 1.2833 (0.5); 1.2646 (1.4); 1.2588 (0.6); 1.2457 (0.5); 1.2193 (0.5); 1.2005 (0.9); 1.1816 (0.5); 1.1397 (0.9); 1.1213 (0.5); 1.1151 (4.9); 1.0963 (9.9); 1.0901 (0.8); 1.0774 (4.5); 0.8818 (1.2); -0.0002 (10.6)
Example No. 1.3-451: 1H-NMR(400.0 MHz, CDC13): δ= 8.6633 (2.5); 8.4067 (2.4); 7.4097 (2.3); 7.2605 (19.9); 6.0143 (1.4); 6.0103 (1.4); 6.0065 (0.5); 2.0953 (16.0); 2.0914 (5.3); 2.0902 (5.2); 2.0874 (5.1); 2.0862 (4.9); 2.0565 (1.2); 1.5433 (5.4); -0.0002 (7.4)
Example No. 1.1-67: 1H-NMR(400.0 MHz, CDC13):
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δ= 7.2608 (37.0); 5.9826 (0.8); 5.9650 (2.1); 5.9612 (2.7); 5.2922 (1.1); 5.2765 (1.5); 5.2609 (1.1); 2.9916 (0.6); 2.9687 (0.6); 2.1645 (5.7); 2.1597 (5.9); 2.1177 (1.8); 2.1164 (1.9); 2.1139 (2.0); 2.1124 (1.9); 1.5731 (2.6); 1.3975 (16.0); 1.3818 (15.9); 1.2557 (1.3); -0.0002 (13.5)
Example No. 1.21-162: 1H-NMR(400.0 MHz, CDC13): δ= 7.2608 (5.7); 6.7172 (2.1); 6.1289 (0.6); 6.1274 (0.6); 6.1191 (0.6); 6.1176 (0.6); 5.9369 (1.1); 4.3820 (0.6); 4.3732 (0.6); 4.3722 (0.6); 1.5912 (0.6); 1.3534 (16.0); 1.3074 (14.2); 1.2979 (0.6); 0.9660 (1.0); 0.0002 (2.1)
Example No. 1.31-162: 1H-NMR(400.0 MHz, CDC13): δ= 7.2620 (5.2); 7.1842 (1.4); 6.6903 (2.2); 6.0060 (1.4); 4.3699 (0.6); 4.3557 (0.6); 4.3519 (0.7); 4.3380 (0.6); 1.5638 (0.6); 1.3716 (1.4); 1.3538 (5.0); 1.3359 (2.0); 1.3305 (16.0); 1.3077 (2.0); 1.2673 (14.7); 0.0002(1.9)
Example No. 1.12-162: 1H-NMR(400.0 MHz, CDC13): δ= 7.2615 (5.0); 6.8512 (1.0); 6.8461 (1.1); 6.7438 (1.1); 6.7387 (1.0); 6.7329 (2.2); 4.3094 (1.3); 4.2916 (1.4); 1.3641 (1.4); 1.3463 (3.2); 1.3381 (16.0); 1.3285 (1.6); 1.2898 (11.4);-0.0002 (2.0)
Example No. 1.1-290: 1H-NMR(400.0 MHz, de-DMSO): δ= 6.2080 (2.2); 6.0345 (0.8); 6.0316 (0.7); 3.3116 (1.2); 2.5051 (3.3); 2.5007 (4.3); 2.4964 (3.1); 2.0450 (2.8); 2.0421 (2.7); 1.2703 (16.0); -0.0002 (1.3)
Example No. 1.1-289: 1H-NMR(400.0 MHz, de-DMSO): δ= 7.1279 (1.3); 7.1065 (1.3); 6.2130 (0.9); 6.1678 (11.2); 6.0352 (3.1); 6.0337 (3.2); 6.0312 (3.2); 6.0297 (3.1); 5.9091 (1.4); 5.8884 (1.3); 5.7527 (1.2); 3.3102 (20.7); 2.9910 (0.7); 2.9737 (1.8); 2.9564 (2.5); 2.9390 (1.9); 2.9217 (0.8); 2.5230 (0.8); 2.5183 (1.2); 2.5096 (12.9); 2.5051 (27.0); 2.5004 (37.2); 2.4959 (25.5); 2.4913 (11.5); 2.0447 (10.7); 2.0436 (11.1); 2.0408 (11.3); 2.0397 (10.6); 1.8529 (0.7); 1.8491 (1.1); 1.8453 (0.7); 1.2282 (15.9); 1.2259 (16.0); 1.2108 (15.4); 1.2086 (15.5); -0.0002 (13.6)
Example No. 1.1-287: 1H-NMR(400.0 MHz, de-DMSO): δ= 7.1423 (2.8); 7.1194 (2.9); 6.1115 (5.5); 6.1110 (5.4); 6.0302 (1.6); 6.0289 (1.6); 6.0262 (1.6); 6.0249 (1.6); 5.9081 (1.3); 5.9068 (1.9); 5.9055 (1.3); 5.8854 (1.3); 5.8840 (1.8); 5.8826 (1.2); 3.3118 (6.5); 2.5098 (3.8); 2.5052 (8.0); 2.5006 (11.1); 2.4961 (7.5); 2.4915 (3.4); 2.2135 (1.6); 2.2095 (0.5); 2.2088 (0.5); 2.2019 (16.0); 2.0441 (6.2); 2.0428 (6.7); 2.0401 (6.5); 2.0388 (6.4); 1.8491 (0.7); -0.0002 (4.1)
Example No. 1.5-290: 1H-NMR(400.0 MHz, CDC13): δ= 7.2627 (4.3); 7.1531 (0.7); 7.1517 (0.9); 6.2931 (2.1); 2.4893 (0.5); 2.4703 (0.5); 2.4576 (0.5); 2.4388 (0.5); 2.0648 (1.8); 2.0634 (1.9); 2.0607 (1.9); 2.0594 (1.8); 1.5643 (0.7); 1.3265 (16.0); 1.2164 (1.4); 1.1976 (2.9); 1.1787 (1.3); -0.0002 (1.6)
Example No. 1.3-290: 1H-NMR(400.0 MHz, CDC13): δ= 7.2627 (4.1); 7.1359 (0.9); 6.2987 (2.0); 6.0302 (0.5); 2.1954 (5.9); 2.0716 (2.0); 2.0687 (2.0); 2.0676 (1.9); 1.5635 (0.6); 1.3299 (16.0); -0.0002 (1.6)
Example No. 1.11-290: 1H-NMR(400.0 MHz, CDC13): δ= 7.2622 (4.4); 6.9617 (1.0); 6.2896 (2.0); 6.0348 (0.5); 6.0337 (0.5); 6.0308 (0.5); 4.3401 (1.2); 4.3222 (1.2); 2.1224 (2.0); 2.1212 (2.0); 2.1184 (2.1); 2.1174 (1.9); 1.5590 (0.7); 1.3786 (1.4); 1.3608 (2.9); 1.3429 (1.5); 1.3274 (16.0); -0.0002 (1.7)
Example No. 1.6-290: 1H-NMR(400.0 MHz, CDC13): δ= 7.2627 (4.1); 7.0050 (0.5); 6.8195 (0.7); 6.3402 (2.0); 2.4410 (0.5); 2.4220 (0.5); 2.4007 (0.5); 2.3819 (0.5); 2.0018 (1.6); 1.9981 (2.5); 1.9944 (1.6); 1.5654 (1.0); 1.3356 (16.0); 1.3259 (1.5); 1.1858 (1.4); 1.1670 (2.8); 1.1481 (1.3); -0.0002 (1.5)
Example No. 1.5-287: 1H-NMR(400.0 MHz, CDC13): δ= 7.2631 (12.6); 7.1555 (3.1); 6.2185 (4.6); 6.0315 (0.8); 6.0289 (1.6); 6.0276 (1.7); 6.0248 (1.7); 6.0234 (1.7); 2.4831 (0.6); 2.4664 (1.0); 2.4641 (2.0); 2.4478 (2.2); 2.4451 (2.2); 2.4290 (2.1); 2.4263 (1.0); 2.4103 (0.7); 2.2716 (16.0); 2.0715 (6.2); 2.0702 (7.0); 2.0675 (6.7); 2.0661 (6.6); 1.5755 (1.0); 1.2179 (4.7); 1.1990 (9.4); 1.1801 (4.4); -0.0002 (4.6)
Example No. 1.3-287: 1H-NMR(400.0 MHz, CDC13): δ= 7.2629 (9.8); 7.1394 (1.8); 7.1381 (2.3); 6.2217 (3.5); 6.0337 (0.5); 6.0311 (1.2); 6.0298 (1.2); 6.0270 (1.2); 6.0257 (1.2); 6.0231 (0.5); 2.2749 (12.7); 2.1833 (16.0); 2.0782 (4.9); 2.0768 (5.2); 2.0742 (5.1); 2.0728 (4.8); 1.5702 (1.5); -0.0002 (3.8)
Example No. 1.11-287: 1H-NMR(400.0 MHz, CDC13):
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Example No. 1.3-289: 1H-NMR(400.0 MHz, CDC13):
δ= 7.2624 (13.1); 7.1398 (1.9); 7.1385 (2.4); 6.2609 (4.2); 6.0323 (1.3); 6.0309 (1.3); 6.0282 (1.3); 6.0269 (1.2); 5.2993 (8.8); 3.0289 (0.8); 3.0115 (1.1); 2.9941 (0.8); 2.1911 (16.0); 2.0757 (5.0); 2.0743 (5.2) ; 2.0716 (5.3); 2.0703 (4.7); 1.5631 (1.9); 1.3019 (7.5); 1.2982 (7.3); 1.2846 (7.5); 1.2808 (7.1); -
0.0002 (5.1)__________________________________________________________________________________________
Example No. 1.81-162: 1H-NMR(400.0 MHz, CDC13):
δ= 7.7713 (0.7); 7.7632 (0.8); 7.7544 (0.8); 7.7475 (0.8); 7.4810 (1.5); 7.4729 (1.6); 7.4650 (1.4); 7.2594 (3.6) ; 6.7860 (1.9); 6.5529 (0.8); 6.5434 (0.8); 6.5092 (1.6); 4.6193 (0.7); 4.6098 (0.8); 1.6168 (0.5);
1.3785 (16.0); -0.0002 (1,3)_______________________________________________________________________________
Example No. 1.1-697: 1H-NMR(400.0 MHz, CDC13):
δ= 7.2611 (36.6); 6.7636 (0.5); 6.2847 (1.4); 6.2513 (9.1); 6.1473 (1.1); 6.1361 (1.1); 6.0288 (2.4); 6.0131 (2.0); 5.9556 (2.6); 5.9541 (2.6); 5.9517 (2.7); 5.9502 (2.5); 2.5370 (1.2); 2.5275 (5.3); 2.5195 (1.7) ; 2.5099 (6.6); 2.1687 (10.3); 2.1676 (10.9); 2.1648 (11.0); 2.1638 (10.4); 2.0567 (0.8); 2.0397 (1.4) ; 2.0229 (1.8); 2.0060 (1.5); 1.9885 (1.0); 1.9857 (1.5); 1.9818 (2.0); 1.9780 (1.3); 1.5741 (2.6);
1.0384 (0.5); 1.0210 (0.7); 0.9932 (15.6); 0.9896 (16.0); 0.9766 (15.5); 0.9730 (15.6); 0.9552 (1.0); 0.0079 (0.5); -0.0002 (13.8); -0.0085 (0.6)________________________________________________________________
Example No. 1.83-162: 1H-NMR(400.0 MHz, CDC13):
δ= 7.8291 (1.4); 7.8284 (1.4); 7.6532 (0.6); 7.6336 (0.7); 7.4755 (1.2); 7.4711 (1.1); 7.4575 (0.6); 7.2610 (4.2) ; 6.7773 (2.3); 6.5347 (1.3); 5.2984 (1.8); 2.0895 (6.2); 1.5559 (0.5); 1.3601 (16.0); -0.0002 (2.6) Example No.1.85-162: 1H-NMR(400.0 MHz, CDC13):
δ= 7.8493 (1.4); 7.8483 (1.4); 7.6515 (0.5); 7.6322 (0.6); 7.4714 (1.2); 7.4667 (0.9); 7.4585 (0.6); 7.4538 (0.6); 7.2611 (4.2); 6.7681 (2.4); 6.5331 (1.3); 6.5326 (1.2); 5.2983 (1.3); 1.3559 (16.0); 1.1174(1.4); 1.0986 (3.0); 1.0797 (1.3); -0.0002 (2,5)__________________________________________________________________
Example No. 1.89-162: 1H-NMR(400.0 MHz, CDC13):
δ= 7.6879 (0.5); 7.6690 (0.6); 7.6552 (1.4); 7.6542 (1.4); 7.4852 (1.3); 7.4800 (0.9); 7.4722 (0.6); 7.4678 (0.6); 7.2605 (4.7); 6.7616 (2.5); 6.5268 (1.3); 5.2977 (1.7); 1.5524 (0.5); 1.3556 (16.0); 1.3217 (1.5); 1.3039 (3.1); 1.2860 (1.5); -0.0002 (3.0)__________________________________________________________________
Example No. 1.1-560: 1H-NMR(400.0 MHz, CDC13):
δ= 7.2604 (52.2); 6.0801 (2.2); 6.0782 (2.1); 6.0761 (2.2); 6.0460 (2.4); 6.0386 (1.9); 6.0372 (2.4); 4.8070 (2.9); 4.7982 (2.9); 3.2203 (0.8); 3.2030 (2.0); 3.1857 (2.8); 3.1684 (2.1); 3.1511 (0.8); 2.2292 (10.4) ; 2.2278 (10.5); 2.2251 (10.7); 2.2237 (10.0); 1.6069 (3.4); 1.3726 (1.4); 1.3682 (16.0); 1.3659 (15.9); 1.3553 (1.5); 1.3509 (15.8); 1.3486 (15.9); 0.0079 (0.6); -0.0002 (18.9); -0.0085 (0.5)
Example No.l. 1-558: 1H-NMR(400.0 MHz, CDC13):
δ= 7.5185 (0.9); 7.2596 (155.7); 6.9956 (0.9); 6.0829 (1.9); 6.0810 (2.1); 6.0788 (2.0); 6.0769 (2.0); 6.0280 (1.7); 4.7701 (0.9); 4.7632 (0.9); 2.9179 (2.1); 2.8989 (6.8); 2.8800 (7.4); 2.8611 (2.5); 2.2286 (9.2) ; 2.2272 (9.5); 2.2246 (9.6); 2.2231 (9.2); 1.5634 (4.1); 1.3811 (7.7); 1.3680 (0.8); 1.3623 (16.0);
1.3433 (7.5); 0.0080 (1.7); -0.0002 (58.0); -0.0085 (1.6)__________________________________________________
Example No. 1.1-387: 1H-NMR(400.0 MHz, CDC13):
δ= 7.5179 (5.1); 7.3569 (2.1); 7.3398 (5.8); 7.3337 (3.4); 7.3253 (5.5); 7.3215 (10.2); 7.3188 (12.4); 7.3131 (12.8); 7.3067 (8.6); 7.3005 (9.4); 7.2979 (9.3); 7.2883 (5.3); 7.2761 (12.2); 7.2729 (16.3); 7.2684 (15.4); 7.2591 (917.5); 7.2305 (1.0); 7.1132 (1.0); 7.0744 (1.2); 7.0617 (17.6); 6.9950 (5.0); 6.0069 (1.1); 5.9833 (3.8); 5.9752 (4.2); 5.9532 (4.0); 4.8069 (5.2); 4.7987 (5.3); 3.8644 (5.7); 3.7503 (5.2) ; 2.2089 (2.9); 2.2049 (2.8); 2.1587 (15.8); 2.1554 (16.0); 2.1046 (2.7); 2.1006 (2.7); 2.0045 (1.8);
1.5331 (165.8); 0.1465 (1.2); 0,0080 (10.7); -0.0002 (320,4); -0,0085 (8.5); -0.1496 (1.2)________________
Example No. 1.1-86: 1H-NMR(400.0 MHz, CDC13):
δ= 7.9481 (0.8); 7.9382 (4.8); 7.9344 (6.9); 7.9292 (2.2); 7.9213 (3.4); 7.9173 (6.9); 7.9141 (5.6); 7.9083 (1.0); 7.9020 (0.6); 7.5183 (0.9); 7.4495 (2.0); 7.4455 (2.8); 7.4411 (1.4); 7.4280 (7.5); 7.4244 (3.2); 7.4235 (3.3); 7.4131 (3.6); 7.4098 (6.1); 7.4080 (4.4); 7.4037 (1.5); 7.3958 (2.8); 7.3920 (4.7); 7.3884 (2.7); 7.3806 (2.3); 7.3761 (19.7); 7.3665 (1.3); 7.3560 (1.4); 7.3527 (0.8); 7.3091 (0.6); 7.3048 (0.7);
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7.2594 (159.5); 7.2358 (1.0); 7.2238 (1.0); 7.1592 (0.5); 6.9954 (0.9); 6.8154 (0.5); 5.9503 (3.6); 5.9469 (3.5) ; 5.6627 (2.1); 4.1274 (1.2); 4.1095 (1.2); 2.2944 (0.6); 2.2015 (15.2); 2.2002 (15.8); 2.1974 (16.0);
2.1962 (15.2); 2.0409 (5.4); 1.9709 (1.0); 1.9671 (1.6); 1.9632 (1.0); 1.5628 (1.2); 1.4318 (2.6); 1.2833 (0.8); 1.2744 (1.7); 1.2655 (0.8); 1.2566 (3.5); 1.2387 (1.6); 0.0080 (2.7); 0.0065 (1.0); 0.0056 (1.2); 0.0002 (88.6); -0.0066 (2,2); -0,0084 (3.5)________________________________________________________________
Example No. 1.1-72: 1H-NMR(400.0 MHz, CDC13):
δ= 7.5185 (2.1); 7.2596 (345.8); 7.2097 (1.0); 6.9956 (2.0); 6.8994 (4.8); 6.8906 (1.8); 6.8297 (0.6);
6.8153 (0.5); 6.0701 (2.0); 5.6581 (2.4); 3.6993 (0.7); 2.6908 (0.8); 2.4867 (16.0); 2.4746 (3.3); 2.4691 (5.6) ; 2.4365 (2.1); 2.4225 (0.8); 2.2418 (7.9); 2.2381 (8.3); 2.2046 (0.9); 2.0797 (0.5); 2.0165 (1.8);
2.0128 (2.6); 2.0089 (1.7); 1.8039 (0.6); 1.4521 (0.8); 1.4115 (0.6); 1.3579 (0.5); 1.3394 (0.6); 1.3029 (0.7); 1.2826 (0.8); 1.2640 (1.8); 1.2554 (2.3); 1.2458 (1.4); 0.3307 (0.7); 0.2376 (0.6); 0.1571 (0.8);
0.1456 (0.6); 0.0080 (4,7); -0.0002 (147.2); -0,0085 (7.6); -0.1494 (0,6)__________________________________
Example No. El-91: 1H-NMR(400.0 MHz, CDC13):
δ= 8.5337 (5.3); 8.0554 (3.4); 7.5188 (1.2); 7.2931 (0.5); 7.2878 (0.6); 7.2599 (219.6); 7.2333 (1.1);
7.2293 (1.0); 7.2111 (0.6); 6.9959 (1.2); 5.9897 (3.6); 5.9860 (3.7); 5.7489 (6.0); 2.9984 (0.5); 2.9772 (0.6); 2.1955 (15.6); 2.1923 (16.0); 2.0424 (1.0); 1.9920 (0.9); 1.9881 (1.4); 1.9844 (1.0); 1.3789 (0.7);
1.2755 (0.5); 1.2579 (1.4); 1.2508 (0.9); 1.2328 (0.7); 0.1566 (1.0); 0.0079 (2.7); -0.0002 (93.1); -0.0085 (4.3)____________________________________________________________________________________________________________
Example No. 1.1-177: 1H-NMR(400.0 MHz, CDC13):
δ= 7.2602 (13.1); 5.8756 (0.8); 2.1427 (1.8); 2.1398 (1.8); 2.1387 (1.8); 2.0940 (0.5); 2.0844 (5.4);
1.4027 (1.9); 1.3979 (16.0); 1.3769 (0.9); 1.3446 (0.8); -0.0002 (5.6)_____________________________________
Example No. 1.2-177: 1H-NMR(400.0 MHz, CDC13):
δ= 7.2597 (64.8); 6.7656 (1.2); 6.7612 (1.8); 6.7568 (1.2); 6.0209 (0.6); 2.0961 (16.0); 2.0052 (0.8); 1.9775 (4.0); 1.9736 (6.5); 1.9697 (4.0); 1.5493 (1.6); 1.4035 (45.6); 0.0080 (0.8); -0.0002 (23.6); 0.0085 (0.7)_________________________________________________________________________________________
Example No. 1.1-300: 1H-NMR(400.0 MHz, CDC13):
δ= 7.2602 (17.6); 5.9397 (0.5); 5.9356 (0.5); 2.1548 (1.9); 2.1537 (2.1); 2.1509 (2.1); 2.1497 (2.1); 2.0600 (0.7); 2.0503 (6.4); 1.5535 (0.6); 1.3601 (3.0); 1.3547 (1.5); 1.3493 (16.0); 1.3213 (0.7); -0.0002 (7-8)____________________________________________________________________________________________________________
Example No. 1.2-300: 1H-NMR(400.0 MHz, CDC13):
δ= 7.2601 (11.8); 5.9378 (0.7); 5.9338 (0.7); 2.1545 (2.8); 2.1518 (2.5); 2.1507 (2.5); 2.0594 (0.5); 2,0493 (6.0); 1.3546 (1.4); 1,3435 (16.0); -0.0002 (4,4)___________________________________________________
Example No. 1.2-709: 1H-NMR(400.0 MHz, CDC13):
δ= 7.2603 (20.8); 5.9743 (0.8); 5.9728 (0.9); 5.9702 (1.4); 5.9688 (1.5); 5.9661 (1.6); 5.9649 (1.6); 5.9624 (0.8); 2.5721 (16.0); 2.1818 (4.6); 2.1802 (4.1); 2.1779 (4.1); 2.1762 (4.6); -0.0002 (12.4)
The present invention furthermore provides the use of one or more compounds of the formula (I) and/or salts thereof, as defined above, preferably in one of the embodiments identified as preferred or particularly preferred, in particular one or more compounds of the formulae (1.1) to (1.116) and/or salts thereof, in each case as defined above, as herbicide and/or plant growth regulator, preferably in crops of useful plants and/or ornamental plants.
The present invention furthermore provides a method for controlling harmful plants and/or for regulating the growth of plants, characterized in that an effective amount
- of one or more compounds of the formula (I) and/or salts thereof, as defined above, preferably in 10 one of the embodiments identified as preferred or particularly preferred, in particular one or more compounds of the formulae (1.1) to (1.116) and/or salts thereof, in each case as defined above, or
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- of a composition according io the invention, as defined below, is applied to the (harmful) plants, seeds of (harmful) plants, the soil in which or on which the (harmful) plants grow or the area under cultivation.
The present invention also provides a method for controlling unwanted plants, preferably in crops of useful plants, characterized in that an effective amount
- of one or more compounds of the formula (I) and/or salts thereof, as defined above, preferably in one of the embodiments identified as preferred or particularly preferred, in particular one or more compounds of the formulae (1.1) to (1.116) and/or salts thereof, in each case as defined above, or
- of a composition according io the invention, as defined below, is applied io unwanted plants (for example harmful plants such as mono- or dicotyledonous weeds or unwanted crop plants), the seed of the unwanted plants (i.e. plant seeds, for example grains, seeds or vegetative propagation organs such as tubers or shoot parts with buds), the soil in which or on which the unwanted plants grow (for example the soil of crop land or non-crop land) or the area under cultivation (i.e. the area on which the unwanted plants will grow).
The present invention furthermore also provides methods for regulating the growth of plants, preferably of useful plants, characterized in that an effective amount
- of one or more compounds of the formula (I) and/or salts thereof, as defined above, preferably in one of the embodiments identified as preferred or particularly preferred, in particular one or more compounds of the formulae (1.1) to (1.116) and/or salts thereof, in each case as defined above, or
- of a composition according io the invention, as defined below, is applied io the plant, the seed of the plant (i.e. plant seed, for example grains, seeds or vegetative propagation organs such as tubers or shoot parts with buds), the soil in which or on which the plants grow (for example the soil of crop land or non-crop land) or the area under cultivation (i.e. the area on which the plants will grow).
In this context, the compounds according io the invention or the compositions according io the invention can be applied for example by pre-sowing (if appropriate also by incorporation into the soil), preemergence and/or post-emergence processes. Specific examples of some representatives of the
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152 monocotyledonous and dicotyledonous weed flora which can be controlled by the compounds according to the invention are as follows, though there is no intention to restrict the enumeration to particular species.
In a method according to the invention for controlling harmful plants or for regulating the growth of plants, one or more compounds of the formula (1) and/or salts thereof are preferably employed for controlling harmful plants or for regulating growth in crops of useful plants or ornamental plants, where in a preferred embodiment the useful plants or ornamental plants are transgenic plants.
The compounds of the formula (1) according to the invention and/or their salts are suitable for controlling the following genera of monocotyledonous and dicotyledonous harmful plants: Monocotyledonous harmful plants of the genera: Aegilops, Agropyron, Agrostis, Alopecurus, Apera, Avena, Brachiaria, Bromus, Cenchrus, Commelina, Cynodon, Cyperus, Dactyloctenium, Digitaria, Echinochloa, Eleocharis, Eleusine, Eragrostis, Eriochloa, Festuca, Fimbristylis, Heteranthera, Imperata, Ischaemum, Leptochloa, Lolium, Monochoria, Panicum, Paspalum, Phalaris, Phleum, Poa, Rottboellia, Sagittaria, Scirpus, Setaria, Sorghum.
Dicotyledonous harmful plants of the genera: Abutilon, Amaranthus, Ambrosia, Anoda, Anthemis, Aphanes, Artemisia, Atriplex, Bellis, Bidens, Capsella, Carduus, Cassia, Centaurea, Chenopodium, Cirsium, Convolvulus, Datura, Desmodium, Emex, Erysimum, Euphorbia, Galeopsis, Galinsoga, Galium, Hibiscus, Ipomoea, Kochia, Lamium, Lepidium, Lindemia, Matricaria, Mentha, Mercurialis, Mullugo, Myosotis, Papaver, Pharbitis, Plantago, Polygonum, Portulaca, Ranunculus, Raphanus, Rorippa, Rotala, Rumex, Salsola, Senecio, Sesbania, Sida, Sinapis, Solanum, Sonchus, Sphenoclea, Stellaria, Taraxacum, Thlaspi, Trifolium, Urtica, Veronica, Viola, Xanthium.
When the compounds according to the invention are applied to the soil surface before germination of the harmful plants (weed grasses and/or broad-leaved weeds) (pre-emergence method), either the seedlings of the weed grasses or broad-leaved weeds are prevented completely from emerging or they grow until they have reached the cotyledon stage, but then stop growing and eventually, after three to four weeks have elapsed, die completely.
If the active compounds are applied post-emergence to the green parts of the plants, growth stops after the treatment, and the harmful plants remain at the growth stage at the time of application, or they die completely after a certain time, so that in this manner competition by the weeds, which is harmful to the crop plants, is eliminated very early and in a sustained manner.
Although the compounds according to the invention display an outstanding herbicidal activity against monocotyledonous and dicotyledonous weeds, crop plants of economically important crops, for example
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153 dicotyledonous crops of the genera Arachis, Beta, Brassica, Cucumis, Cucurbita, Helianthus, Daucus, Glycine, Gossypium, Ipomoea, Lactuca, Linum, Lycopersicon, Miscanthus, Nicotiana, Phaseolus, Pisum, Solanum, Vicia, or monocotyledonous crops of the genera Allium, Ananas, Asparagus, Avena, Hordeum, Oryza, Panicum, Saccharum, Secale, Sorghum, triticale, triticum, Zea, are damaged only to an insignificant extent, or not at all, depending on the structure of the respective compound according to the invention and its application rate. For these reasons, the present compounds are very suitable for selective control of unwanted plant growth in plant crops such as agriculturally useful plants or ornamental plants.
In addition, the compounds of the invention (depending on their particular structure and the application rate deployed) have outstanding growth-regulating properties in crop plants. They intervene in the plants’ own metabolism with regulatory effect, and can thus be used for the controlled influencing of plant constituents and to facilitate harvesting, for example by triggering desiccation and stunted growth. Furthermore, they are also suitable for the general control and inhibition of unwanted vegetative growth without killing the plants in the process. Inhibition of vegetative growth plays a major role for many mono- and dicotyledonous crops since, for example, this can reduce or completely prevent lodging.
By virtue of their herbicidal and plant growth regulatory properties, the active compounds can also be used to control harmful plants in crops of genetically modified plants or plants modified by conventional mutagenesis. In general, the transgenic plants are characterized by particular advantageous properties, for example by resistances to certain pesticides, in particular certain herbicides, resistances to plant diseases or pathogens of plant diseases, such as certain insects or microorganisms such as fungi, bacteria or viruses. Other specific characteristics relate, for example, to the harvested material with regard to quantity, quality, storability, composition and specific constituents. For instance, there are known transgenic plants with an elevated starch content or altered starch quality, or those with a different fatty acid composition in the harvested material.
It is preferred with a view to transgenic crops to use the compounds according to the invention and/or their salts in economically important transgenic crops of useful plants and ornamentals, for example of cereals such as wheat, barley, rye, oats, millet, rice and com or else crops of sugar beet, cotton, soybean, oilseed rape, potato, tomato, peas and other vegetables.
It is preferred to employ the compounds according to the invention as herbicides in crops of useful plants which are resistant, or have been made resistant by recombinant means, to the phytotoxic effects of the herbicides.
By virtue of their herbicidal and plant growth regulatory properties, the active compounds can also be used to control harmful plants in crops of genetically modified plants which are known or are yet to be
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154 developed. In general, the transgenic plants are characterized by particular advantageous properties, for example by resistances to certain pesticides, in particular certain herbicides, resistances to plant diseases or pathogens of plant diseases, such as certain insects or microorganisms such as fungi, bacteria or viruses. Other specific characteristics relate, for example, to the harvested material with regard to quantity, quality, storability, composition and specific constituents. For instance, there are known transgenic plants with an elevated starch content or altered starch quality, or those with a different fatty acid composition in the harvested material. Further special properties may be tolerance or resistance to abiotic stressors, for example heat, cold, drought, salinity and ultraviolet radiation.
Preference is given to the use of the compounds of the formula (I) according to the invention or salts thereof in economically important transgenic crops of useful plants and ornamental plants, for example of cereals such as wheat, barley, rye, oats, triticale, millet, rice, cassava and com, or else crops of sugar beet, cotton, soybean, oilseed rape, potatoes, tomatoes, peas and other vegetables.
The compounds of the formula (I) can preferably be used as herbicides in crops of useful plants which are resistant, or have been made resistant by recombinant means, to the phytotoxic effects of the herbicides.
Conventional ways of producing novel plants which have modified properties in comparison to existing plants consist, for example, in traditional cultivation methods and the generation of mutants. Alternatively, novel plants with altered properties can be generated with the aid of recombinant methods.
A large number of molecular-biological techniques by means of which novel transgenic plants with modified properties can be generated are known to the person skilled in the art. For such recombinant manipulations, nucleic acid molecules which allow mutagenesis or sequence alteration by recombination of DNA sequences can be introduced into plasmids. With the aid of standard methods, it is possible, for example, to undertake base exchanges, remove parts of sequences or add natural or synthetic sequences. To connect the DNA fragments to each other, adapters or linkers may be added to the fragments.
For example, the generation of plant cells with a reduced activity of a gene product can be achieved by expressing at least one corresponding antisense RNA, a sense RNA for achieving a cosuppression effect, or by expressing at least one suitably constructed ribozyme which specifically cleaves transcripts of the abovementioned gene product.
To this end, it is firstly possible to use DNA molecules which encompass the entire coding sequence of a gene product inclusive of any flanking sequences which may be present, and also DNA molecules which
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155 only encompass portions of the coding sequence, in which case it is necessary for these portions to be long enough to have an antisense effect in the cells. It is also possible to use DNA sequences which have a high degree of homology to the coding sequences of a gene product, but are not completely identical to them.
When expressing nucleic acid molecules in plants, the protein synthesized may be localized in any desired compartment of the plant cell. However, to achieve localization in a particular compartment, it is possible, for example, to join the coding region to DNA sequences which ensure localization in a particular compartment. Such sequences are known to those skilled in the art (see, for example, Braun et al., EMBO J. 11 (1992), 3219-3227). The nucleic acid molecules can also be expressed in the organelles of the plant cells.
The transgenic plant cells can be regenerated by known techniques to give rise to entire plants. In principle, the transgenic plants may be plants of any desired plant species, i.e. not only monocotyledonous but also dicotyledonous plants.
Thus, transgenic plants can be obtained whose properties are altered by overexpression, suppression or inhibition of homologous (= natural) genes or gene sequences or expression of heterologous (= foreign) genes or gene sequences.
It is preferred to employ the compounds (I) according to the invention in transgenic crops which are resistant to growth regulators such as, for example, dicamba, or to herbicides which inhibit essential plant enzymes, for example acetolactate synthases (ALS), EPSP synthases, glutamine synthases (GS) or hydroxyphenylpyruvate dioxygenases (HPPD), or to herbicides from the group of the sulfonylureas, glyphosate, glufosinate or benzoylisoxazoles and analogous active compounds.
When the active compounds of the invention are employed in transgenic crops, not only do the effects toward harmful plants observed in other crops occur, but frequently also effects which are specific to application in the particular transgenic crop, for example an altered or specifically widened spectrum of weeds which can be controlled, altered application rates which can be used for the application, preferably good combinability with the herbicides to which the transgenic crop is resistant, and influencing of growth and yield of the transgenic crop plants.
The invention therefore also relates to the use of the compounds of the formula (I) according to the invention and/or their salts as herbicides for controlling harmful plants in crops of useful plants or ornamentals, optionally in transgenic crop plants.
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Preference is given io the use in cereals, here preferably com, wheat, barley, rye, oats, millet or rice, by the pre- or post-emergence method.
Preference is also given io the use in soybeans by the pre- or post-emergence method.
The use according io the invention for the control of harmful plants or for growth regulation of plants also includes the case in which the active compound of the formula (1) or its salt is not formed from a precursor substance (“prodrug”) until after application on the plant, in the plant or in the soil.
The invention also provides for the use of one or more compounds of the formula (1) or salts thereof or of a composition according io the invention (as defined below) (in a method) for controlling harmful plants or for regulating the growth of plants which comprises applying an effective amount of one or more compounds of the formula (I) or salts thereof onto the plants (harmful plants, if appropriate together with the useful plants), plant seeds, the soil in which or on which the plants grow or the area under cultivation.
The invention also provides a herbicidal and/or plant growth-regulating composition, characterized in that the composition comprises (a) one or more compounds of the formula (I) and/or salts thereof, as defined above, preferably in one of the embodiments identified as preferred or particularly preferred, in particular one or more compounds of the formulae (1.1) to (1.116) and/or salts thereof, in each case as defined above, and (b) one or more further substances selected from groups (i) and/or (ii):
(i) one or more further agrochemically active substances, preferably selected from the group consisting of insecticides, acaricides, nematicides, further herbicides (i.e. those not corresponding to the formula (I) defined above), fungicides, safeners, fertilizers and/or further growth regulators, (ii) one or more formulation auxiliaries customary in crop protection.
Here, the further agrochemically active substances of component (i) of a composition according to the invention are preferably selected from the group of substances mentioned in The Pesticide Manual, 16th edition, The British Crop Protection Council and the Royal Soc. of Chemistry, 2012.
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A herbicidal or plant growth-regulating composition according to the invention comprises preferably one, two, three or more formulation auxiliaries (ii) customary in crop protection selected from the group consisting of surfactants, emulsifiers, dispersants, film-formers, thickeners, inorganic salts, dusting agents, carriers solid at 25°C and 1013 mbar, preferably adsorbant granulated inert materials, wetting agents, antioxidants, stabilizers, buffer substances, antifoam agents, water, organic solvents, preferably organic solvents miscible with water in any ratio at 25°C and 1013 mbar.
The compounds (1) according to the invention can be used in the form of wettable powders, emulsifiable concentrates, sprayable solutions, dusting products or granules in the customary formulations. The invention therefore also provides herbicidal and plant growth-regulating compositions which comprise compounds of the formula (I) and/or salts thereof.
The compounds of the formula (I) and/or salts thereof can be formulated in various ways according to which biological and/or physicochemical parameters are required. Possible formulations include, for example: wettable powders (WP), water-soluble powders (SP), water-soluble concentrates, emulsifiable concentrates (EC), emulsions (EW), such as oil-in-water and water-in-oil emulsions, sprayable solutions, suspension concentrates (SC), dispersions based on oil or water, oil-miscible solutions, capsule suspensions (CS), dusting products (DP), dressings, granules for scattering and soil application, granules (GR) in the form of microgranules, spray granules, absorption and adsorption granules, waterdispersible granules (WG), water-soluble granules (SG), ULV formulations, microcapsules and waxes.
These individual formulation types and the formulation assistants, such as inert materials, surfactants, solvents and further additives, are known to the person skilled in the art and are described, for example, in: Watkins, Handbook of Insecticide Dust Diluents and Carriers, 2nd Ed., Darland Books, Caldwell N.J.; H.v. Olphen, Introduction to Clay Colloid Chemistry, 2nd ed., J. Wiley & Sons, N.Y.; C. Marsden, Solvents Guide, 2nd ed., Interscience, N.Y. 1963; McCutcheon's Detergents and Emulsifiers Annual, MC Publ. Corp., Ridgewood N.J.; Sisley and Wood, Encyclopedia of Surface Active Agents, Chem. Publ. Co. Inc., N.Y. 1964; Schonfeldt, Grenzflachenaktive Athylenoxidaddukte [Interface-active Ethylene Oxide Adducts], Wiss. Verlagsgesellschaft, Stuttgart 1976; Winnacker-Kuchler, Chemische Technologie [Chemical Technology], volume 7, C. Hanser Verlag Munich, 4th Ed. 1986.
Wettable powders are preparations which can be dispersed uniformly in water and, in addition to the active compound, apart from a diluent or inert substance, also comprise surfactants of the ionic and/or nonionic type (wetting agents, dispersants), for example polyoxyethylated alkylphenols, polyoxyethylated fatty alcohols, polyoxyethylated fatty amines, fatty alcohol polyglycol ether sulfates, alkanesulfonates, alkylbenzenesulfonates, sodium lignosulfonate, sodium 2,2'-dinaphthylmethane-6,6'
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158 disulfonate, sodium dibutylnaphthalenesulfonate or else sodium oleoylmethyltaurate. To produce the wettable powders, the herbicidally active compounds are finely ground, for example in customary apparatuses such as hammer mills, blower mills and air-jet mills, and simultaneously or subsequently mixed with the formulation auxiliaries.
Emulsifiable concentrates are produced by dissolving the active compound in an organic solvent, for example butanol, cyclohexanone, dimethylformamide, xylene, or else relatively high-boiling aromatics or hydrocarbons or mixtures of the organic solvents, with addition of one or more ionic and/or nonionic surfactants (emulsifiers). Examples of emulsifiers which may be used are: calcium alkylarylsulfonates such as calcium dodecylbenzenesulfonate, or nonionic emulsifiers such as fatty acid polyglycol esters, alkylaryl polyglycol ethers, fatty alcohol polyglycol ethers, propylene oxide-ethylene oxide condensation products, alkyl polyethers, sorbitan esters, for example sorbitan fatty acid esters, or polyoxyethylene sorbitan esters, for example polyoxyethylene sorbitan fatty acid esters.
Dusting products are obtained by grinding the active compound with finely distributed solids, for example talc, natural clays, such as kaolin, bentonite and pyrophyllite, or diatomaceous earth.
Suspension concentrates may be water- or oil-based. They may be prepared, for example, by wetgrinding by means of commercial bead mills and optional addition of surfactants as have, for example, already been listed above for the other formulation types.
Emulsions, for example oil-in-water emulsions (EW), can be produced, for example, by means of stirrers, colloid mills and/or static mixers using aqueous organic solvents and optionally surfactants as already listed above, for example, for the other formulation types.
Granules can be produced either by spraying the active compound onto adsorptive granular inert material or by applying active compound concentrates to the surface of carriers, such as sand, kaolinites or granular inert material, by means of adhesives, for example polyvinyl alcohol, sodium polyacrylate or else mineral oils. Suitable active compounds can also be granulated in the manner customary for the production of fertilizer granules - if desired as a mixture with fertilizers.
Water-dispersible granules are produced generally by the customary processes such as spray-drying, fluidized-bed granulation, pan granulation, mixing with high-speed mixers and extrusion without solid inert material.
For the production of pan, fluidized-bed, extruder and spray granules, see e.g. processes in Spray Drying Handbook 3rd Ed. 1979, G. Goodwin Ltd., London, J.E. Browning, Agglomeration, Chemical
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159 and Engineering 1967, pages 147 ff; Perry's Chemical Engineer's Handbook, 5th Ed., McGraw Hill, New York 1973, p. 8-57.
For further details regarding the formulation of crop protection compositions, see, for example, G.C. Klingman, Weed Control as a Science, John Wiley and Sons, Inc., New York, 1961, pages 81-96 and J.D. Freyer, S.A. Evans, Weed Control Handbook, 5th Ed., Blackwell Scientific Publications, Oxford, 1968, pages 101-103.
The agrochemical preparations, preferably herbicidal or plant growth-regulating compositions, of the present invention preferably comprise a total amount of from 0.1 to 99% by weight, preferably 0.5 to 95% by weight, particularly preferably 1 to 90% by weight, especially preferably 2 to 80% by weight, of active compounds of the formula (I) and their salts.
In wettable powders, the active compound concentration is, for example, about 10 to 90% by weight, the remainder to 100% by weight consisting of customary formulation constituents. In emulsifiable concentrates, the active compound concentration may be about 1% to 90% and preferably 5% to 80% by weight. Formulations in the form of dusts comprise 1% to 30% by weight of active compound, preferably usually 5% to 20% by weight of active compound; sprayable solutions contain about 0.05% to 80% by weight, preferably 2% to 50% by weight of active compound. In the case of water-dispersible granules, the active compound content depends partially on whether the active compound is in liquid or solid form and on which granulation auxiliaries, fillers, etc., are used. In the water-dispersible granules, the content of active compound is, for example, between 1 % and 95% by weight, preferably between 10% and 80% by weight.
In addition, the active compound formulations mentioned optionally comprise the respective customary stickers, wetters, dispersants, emulsifiers, penetrants, preservatives, antifreeze agents and solvents, fillers, carriers and dyes, defoamers, evaporation inhibitors and agents which influence the pH and the viscosity. Examples of formulation auxiliaries are described inter alia in “Chemistry and Technology of Agrochemical Formulations”, ed. D.A. Knowles, Kluwer Academic Publishers (1998).
The compounds of the formula (I) or salts thereof can be used as such or in the form of their preparations (formulations) in a combination with other pesticidally active substances, for example insecticides, acaricides, nematicides, herbicides, fungicides, safeners, fertilizers and/or growth regulators, for example in the form of a finished formulation or of a tank mix. The combination formulations can be prepared on the basis of the abovementioned formulations, while taking account of the physical properties and stabilities of the active compounds to be combined.
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Active compounds which can be employed in combination with the compounds of formula (I) according to the invention in mixture formulations or in a tank mix are, for example, known active compounds based on inhibition of, for example, acetolactate synthase, acetyl-CoA carboxylase, cellulose synthase, enolpyruvylshikimate-3-phosphate synthase, glutamine synthetase, p-hydroxyphenylpyruvate dioxygenase, phytoendesaturase, photosystem I, photosystem II, protoporphyrinogen oxidase, as described, for example, in Weed Research 26 (1986) 441-445 or The Pesticide Manual, 16th edition, The British Crop Protection Council and the Royal Soc. of Chemistry, 2012 and literature cited therein.
Of particular interest is the selective control of harmful plants in crops of useful plants and ornamentals. Although the compounds (I) according to the invention have already demonstrated very good to adequate selectivity in a large number of crops, in principle, in some crops and in particular also in the case of mixtures with other, less selective herbicides, phytotoxicities on the crop plants may occur. In this connection, combinations of compounds (I) according to the invention are of particular interest which comprise the compounds (I) or their combinations with other herbicides or pesticides and safeners. The safeners, which are used in an antidotically effective amount, reduce the phytotoxic side effects of the herbicides/pesticides employed, for example in economically important crops, such as cereals (wheat, barley, rye, com, rice, millet), sugarbeet, sugarcane, oilseed rape, cotton and soybeans, preferably cereals.
The weight ratios of herbicide (mixture) to safener depend generally on the herbicide application rate and the efficacy of the safener in question and may vary within wide limits, for example in the range from 200:1 to 1:200, preferably 100:1 to 1:100, in particular 20:1 to 1:20. Analogously to the compounds (I) or mixtures thereof, the safeners can be formulated with further herbicides/pesticides and be provided and employed as a finished formulation or tank mix with the herbicides.
For application, the herbicide or herbicide/safener formulations present in commercial form are, if appropriate, diluted in a customary manner, for example in the case of wettable powders, emulsifiable concentrates, dispersions and water-dispersible granules with water. Dust-type preparations, granules for soil application or granules for scattering and sprayable solutions are not normally diluted further with other inert substances prior to application.
The application rate of the compounds of the formula (I) and/or their salts is affected to a certain extent by external conditions such as temperature, humidity, etc. Here, the application rate may vary within wide limits. For the application as a herbicide for controlling harmful plants, the total amount of compounds of the formula (I) and their salts is preferably in the range from 0.001 to 10.0 kg/ha, with preference in the range from 0.005 to 5 kg/ha, more preferably in the range from 0.01 to 1.5 kg/ha, in
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161 particular preferably in the range from 0.05 to 1 kg/ha. This applies both to the pre-emergence and the post-emergence application.
When the compounds of the formula (I) and/or their salts are used as plant growth regulator, for example as culm stabilizer for crop plants like those mentioned above, preferably cereal plants, such as wheat, barley, rye, triticale, millet, rice or com, the total application rate is preferably in the range of from 0.001 to 2 kg/ha, preferably in the range of from 0.005 to 1 kg/ha, in particular in the range of from 10 to 500 g/ha, very particularly in the range from 20 to 250 g/ha. This applies both to the pre-emergence and the post-emergence application.
The application as culm stabilizer may take place at various stages of the growth of the plants. Preferred is, for example, the application after the tillering phase, at the beginning of the longitudinal growth.
As an alternative, application as plant growth regulator is also possible by treating the seed, which includes various techniques for dressing and coating seed. Here, the application rate depends on the particular techniques and can be determined in preliminary tests.
Active compounds which can be employed in combination with the compounds of the formula (I) according to the invention in compositions according to the invention (for example in mixed formulations or in the tank mix) are, for example, known active compounds which are based on the inhibition of, for example, acetolactate synthase, acetyl-CoA carboxylase, cellulose synthase, enolpyruvylshikimate-3-phosphate synthase, glutamine synthetase, p-hydroxyphenylpyruvate dioxygenase, phytoene desaturase, photosystem I, photosystem II, protoporphyrinogen oxidase, as are described in, for example, Weed Research 26 (1986) 441-445 or The Pesticide Manual, 16th edition, The British Crop Protection Council and the Royal Soc. of Chemistry, 2012 and the literature cited therein. Known herbicides or plant growth regulators which can be combined with the compounds according to the invention are, for example, the following active compounds, where the compounds are designated either with the common name in accordance with the International Organization for Standardization (ISO) or with the chemical name or with the code number. They always encompass all of the application forms such as, for example, acids, salts, esters and also all isomeric forms such as stereoisomers and optical isomers, even if not explicitly mentioned.
Examples of such herbicidal mixing partners are:
acetochlor, acifluorfen, acifluorfen-sodium, aclonifen, alachlor, allidochlor, alloxydim, alloxydimsodium, ametryn, amicarbazone, amidochlor, amidosulfuron, 4-amino-3-chloro-6-(4-chloro-2-fluoro-3metiiylphenyl)-5-fluoropyridine-2-carboxylic acid, aminocyclopyrachlor, aminocyclopyrachlorpotassium, aminocyclopyrachlor-methyl, aminopyralid, amitrole, ammoniumsulfamate, anilofos,
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162 asulam, atrazine, azafenidin, azimsulfuron, beflubutamid, benazolin, benazolin-ethyl, benfluralin, benfuresate, bensulfiiron, bensulfiiron-methyl, bensulide, bentazone, benzobicyclon, benzofenap, bicyclopyron, bifenox, bilanafos, bilanafos-sodium, bispyribac, bispyribac-sodium, bromacil, bromobutide, bromofenoxim, bromoxynil, bromoxynil-butyrate, -potassium, -heptanoate and -octanoate, busoxinone, butachlor, butafenacil, butamifos, butenachlor, butralin, butroxydim, butylate, cafenstrole, carbetamide, carfentrazone, carfentrazone-ethyl, chloramben, chlorbromuron, chlorfenac, chlorfenacsodium, chlorfenprop, chlorflurenol, chlorflurenol-methyl, chloridazon, chlorimuron, chlorimuron-ethyl, chlorophthalim, chlorotoluron, chlorthal-dimethyl, chlorsulfuron, cinidon, cinidon-ethyl, cinmethylin, cinosulfuron, clacyfos, clethodim, clodinafop, clodinafop-propargyl, clomazone, clomeprop, clopyralid, cloransulam, cloransulam-methyl, cumyluron, cyanamide, cyanazine, cycloate, cyclopyrimorate, cyclosulfamuron, cycloxydim, cyhalofop, cyhalofop-butyl, cyprazine, 2,4-D, 2,4-D-butotyl, -butyl, dimethylammonium, -diolamine, -ethyl, 2-ethylhexyl, -isobutyl, -isooctyl, -isopropylammonium, potassium, -triisopropanolammonium and -trolamine, 2,4-DB, 2,4-DB-butyl, -dimethylammonium, isooctyl, -potassium and -sodium, daimuron (dymron), dalapon, dazomet, n-decanol, desmedipham, detosyl-pyrazolate (DTP), dicamba, dichlobenil, 2-(2,4-dichlorobenzyl)-4,4-dimethyl-l,2-oxazolidin-3one, 2-(2,5-dichlorobenzyl)-4,4-dimethyl-l,2-oxazolidin-3-one, dichlorprop, dichlorprop-P, diclofop, diclofop-methyl, diclofop-P-methyl, diclosulam, difenzoquat, diflufenican, diflufenzopyr, diflufenzopyrsodium, dimefuron, dimepiperate, dimethachlor, dimethametryn, dimethenamid, dimethenamid-P, dimetrasulfuron, dinitramine, dinoterb, diphenamid, diquat, diquat-dibromid, dithiopyr, diuron, DNOC, endothal, EPTC, esprocarb, ethalfluralin, ethametsulfuron, ethametsulfuron-methyl, ethiozin, ethofumesate, ethoxyfen, ethoxyfen-ethyl, ethoxysulfuron, etobenzanid, F-9600, F-5231, i.e. N-[2chloro-4-fluoro-5-[4-(3-fluoropropyl)-4,5-dihydro-5-oxo-lH-tetrazol-l-ylphenyl]ethanesulfonamide, F7967, i.e. 3-[7-chloro-5-fluoro-2-(trifluoromethyl)-lH-benzimidazol-4-yl]-l-methyl-6(trifluoromethyl)pyrimidine-2,4(lH,3H)-dione, fenoxaprop, fenoxaprop-P, fenoxaprop-ethyl, fenoxaprop-P-ethyl, fenoxasulfone, fenquinotrione, fentrazamide, flamprop, flamprop-M-isopropyl, flamprop-M-methyl, flazasulfuron, florasulam, fluazifop, fluazifop-P, fluazifop-butyl, fluazifop-P-butyl, flucarbazone, flucarbazone-sodium, flucetosulfuron, fluchloralin, flufenacet, flufenpyr, flufenpyr-ethyl, flumetsulam, flumiclorac, flumiclorac-pentyl, flumioxazin, fluometuron, flurenol, flurenol-butyl, dimethylammonium and -methyl, fluoroglycofen, fluoroglycofen-ethyl, flupropanate, flupyrsulfuron, fhipyrsulfuron-methyl-sodium, fluridone, flurochloridone, fluroxypyr, fluroxypyr-meptyl, flurtamone, fluthiacet, fluthiacet-methyl, fomesafen, fomesafen-sodium, foramsulfuron, fosamine, glufosinate, glufosinate-ammonium, glufosinate-P-sodium, glufosinate-P-ammonium, glufosinate-P-sodium, glyphosate, glyphosate-ammonium, -isopropylammonium, -diammonium, -dimethylammonium, potassium, -sodium and -trimesium, H-9201, i.e. O-2,4-dimethyl-6-nitrophenyl O-ethyl isopropylphosphoramidothioate, halauxifen, halauxifen-methyl, halosafen, halosulfuron, halosulfuronmethyl, haloxyfop, haloxyfop-P, haloxyfop-ethoxyethyl, haloxyfop-P-ethoxyethyl, haloxyfop-methyl, haloxyfop-P-methyl, hexazinone, HW-02, i.e. l-(dimethoxyphosphoryl)ethyl (2,4
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163 dichlorophenoxy)acetate, imazamethabenz, imazamethabenz-methyl, imazamox, imazamox-ammonium, imazapic, imazapic-ammonium, imazapyr, imazapyr-isopropylammonium, imazaquin, imazaquinammonium, imazethapyr, imazethapyr-immonium, imazosulfuron, indanofan, indaziflam, iodosulfuron, iodosulfuron-methyl-sodium, ioxynil, ioxynil-ocianoaie, -potassium and sodium, ipfencarbazone, isoproturon, isouron, isoxaben, isoxaflutole, karbutilate, KUH-043, i.e. 3-({[5-(difluoromethyl)-lmethyl-3-(trifluoromethyl)-lH-pyrazol-4-yl]methyl}sulfonyl)-5,5-dimethyl-4,5-dihydro-l,2-oxazole, ketospiradox, lactofen, lenacil, linuron, MCPA, MCPA-butotyl, -dimethylammonium, -2-ethylhexyl, isopropylammonium, -potassium and -sodium, MCPB, MCPB-methyl, -ethyl and -sodium, mecoprop, mecoprop-sodium and -butotyl, mecoprop-P, mecoprop-P-butotyl, -dimethylammonium, -2-ethylhexyl and -potassium, mefenacet, mefluidide, mesosulfuron, mesosulfuron-methyl, mesotrione, methabenzthiazuron, metam, metamifop, metamitton, metazachlor, metazosulfuron, methabenzthiazuron, methiopyrsulfuron, methiozolin, methyl isothiocyanate, metobromuron, metolachlor, S-metolachlor, metosulam, metoxuron, mettibuzin, metsulfuron, metsulfuron-methyl, molinat, monolinuron, monosulfuron, monosulfuron-ester, MT-5950, i.e. N-[3-chloro-4-(lmethylethyl)phenyl]-2-metiiylpentanamide, NGGC-011, napropamide, NC-310, i.e. 4-(2,4dichlorobenzoyl)-l-methyl-5-benzyloxypyrazole, neburon, nicosulfuron, nonanoic acid (pelargonic acid), norflurazon, oleic acid (fatty acids), orbencarb, orthosulfamuron, oryzalin, oxadiargyl, oxadiazon, oxasulfuron, oxaziclomefon, oxyfluorfen, paraquat, paraquat dichloride, pebulate, pendimethalin, penoxsulam, pentachlorophenol, pentoxazone, pethoxamid, petroleum oils, phenmedipham, picloram, picolinafen, pinoxaden, piperophos, pretilachlor, primisulfuron, primisulfuron-methyl, prodiamine, profoxydim, prometon, promettyn, propachlor, propanil, propaquizafop, propazine, propham, propisochlor, propoxycarbazone, propoxycarbazone-sodium, propyrisulfuron, propyzamide, prosulfocarb, prosulfuron, pyraclonil, pyraflufen, pyraflufen-ethyl, pyrasulfotole, pyrazolynate (pyrazolate), pyrazosulfuron, pyrazosulfuron-ethyl, pyrazoxyfen, pyribambenz, pyribambenz-isopropyl, pyribambenz-propyl, pyribenzoxim, pyributicarb, pyridafol, pyridate, pyriftalid, pyriminobac, pyriminobac-methyl, pyrimisulfan, pyrithiobac, pyrithiobac-sodium, pyroxasulfone, pyroxsulam, quinclorac, quinmerac, quinoclamine, quizalofop, quizalofop-ethyl, quizalofop-P, quizalofop-P-ethyl, quizalofop-P-tefuryl, rimsulfuron, saflufenacil, sethoxydim, siduron, simazine, simettyn, SL-261, sulcottione, sulfenttazone, sulfomettiron, sulfomettiron-methyl, sulfosulfuron, SYN-523, SYP-249, i.e. 1-ethoxy-3-methyl-l-oxobut-3-en-2-yl 5-[2-chloro-4-(ttifluoromethyl)phenoxy]-2-nitrobenzoate, SYP300, i.e. l-[7-fluoro-3-oxo-4-(prop-2-yn-l-yl)-3,4-dihydro-2H-l,4-benzoxazin-6-yl]-3-propyl-2thioxoimidazolidine-4,5-dione, 2,3,6-TBA, TCA (trifluoroacetic acid), TCA-sodium, tebuthiuron, tefuryltrione, tembottione, tepraloxydim, terbacil, terbucarb, terbumeton, terbuthylazin, terbutryn, thenylchlor, thiazopyr, thiencarbazone, thiencarbazone-methyl, thifensulfuron, thifensulfuron-methyl, thiobencarb, tiafenacil, tolpyralate, topramezone, tralkoxydim, ttiafamone, tti-allate, triasulfuron, ttiaziflam, ttibenuron, ttibenuron-methyl, tticlopyr, trietazine, ttifloxysulfuron, ttifloxysulfuron-sodium, ttifludimoxazin, trifluralin, ttiflusulfuron, triflusulfuron-mcthyl, ttitosulfuron, urea sulfate, vernolate,
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XDE-848, ZJ-0862, i.e. 3,4-dichloro-N-{2-[(4,6-dimethoxypyrimidin-2-yl)oxy]benzyl} aniline, and also the following compounds:
Figure AU2017379281A1_D0216
Examples of plant growth regulators as possible mixing partners are:
acibenzolar, acibenzolar-S-methyl, 5-aminolevulinic acid, ancymidol, 6-benzylaminopurine, brassinolide, catechol, chlormequat chloride, cloprop, cyclanilide, 3-(cycloprop-1-enyl)propionic acid, daminozide, dazomet, n-decanol, dikegulac, dikegulac-sodium, endothal, endothal-dipotassium, disodium, and mono(N,N-dimethylalkylammonium), ethephon, flumetralin, flurenol, flurenol-butyl, flurprimidol, forchlorfenuron, gibberellic acid, inabenfide, indole-3-acetic acid (1AA), 4-indol-3ylbutyric acid, isoprotitiolane, probenazole, jasmonic acid, jasmonic acid methyl ester, maleic hydrazide, mepiquat chloride, 1-methylcyclopropene, 2-(l-naphthyl)acetamide, 1-naphthylacetic acid, 2naphthyloxyacetic acid, nitrophenoxide mixture, 4-oxo-4[(2-phenylethyl)amino]butyric acid, paclobutrazole, N-phenylphthalamic acid, prohexadione, prohexadione-calcium, prohydrojasmone, salicylic acid, strigolactone, tecnazene, titidiazuron, triacontanol, trinexapac, trinexapac-ethyl, tsitodef, uniconazole, uniconazole-P.
Suitable combination partners for the compounds of the formula (1) according to the invention also include, for example, the following safeners:
SI) Compounds from the group of heterocyclic carboxylic acid derivatives:
S1a) Compounds of the dichlorophenylpyrazoline-3-carboxylic acid type (S1a), preferably compounds such as
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1- (2,4-dichlorophenyl)-5-(ethoxycarbonyl)-5-methyl-2-pyrazoline-3-carboxylic acid, ethyl 1(2,4-dichlorophenyl)-5-(ethoxycarbonyl)-5-methyl-2-pyrazoline-3-carboxylate (Sl-1) (mefenpyr-diethyl), and related compounds as described in WO-A-91/07874;
Slb) Derivatives of dichlorophenylpyrazolecarboxylic acid (Slb), preferably compounds such as ethyl 1-(2,4-dichlorophenyl)-5-methylpyrazole-3-carboxylate (Sl-2), ethyl 1-(2,4dichlorophenyl)-5-isopropylpyrazole-3-carboxylate (Sl-3), ethyl 1-(2,4-dichloropheny 1)-5-( 1,1dimethylethyl)pyrazole-3-carboxylate (SI-4) and related compounds as described in EP-A333131 131 and EP-A-269806;
Slc) Derivatives of l,5-diphenylpyrazole-3-carboxylic acid (Slc), preferably compounds such as ethyl l-(2,4-dichlorophenyl)-5-phenylpyrazole-3-carboxylate (SI-5), methyl 1-(2chlorophenyl)-5-phenylpyrazole-3-carboxylate (SI-6) and related compounds as described, for example, in EP-A-268554;
Sld) Compounds of the triazolecarboxylic acid type (S1d), preferably compounds such as fenchlorazole (ethyl ester), i.e. ethyl 1 -(2,4-dichlorophenyl)-5-trichloromethyl-1H-1,2,4ttiazole-3-carboxylate (Sl-7), and related compounds, as described in EP-A-174562 and EP-A346620;
Sle) Compounds of the 5-benzyl- or 5-phenyl-2-isoxazoline-3-carboxylic acid or of the 5,5-diphenyl-
2- isoxazoline-3-carboxylic acid type (S1e), preferably compounds such as ethyl 5-(2,4dichlorobenzyl)-2-isoxazoline-3-carboxylate (Sl-8) or ethyl 5-phenyl-2-isoxazoline-3carboxylate (Sl-9) and related compounds as described in WO-A-91/08202, or 5,5-diphenyl-2isoxazolinecarboxylic acid (Sl-10) or ethyl 5,5-diphenyl-2-isoxazoline-3-carboxylate (Sl-11) (isoxadifen-ethyl) or n-propyl 5,5-diphenyl-2-isoxazoline-3-carboxylate (S1-12) or ethyl 5-(4fluorophenyl)-5-phenyl-2-isoxazoline-3-carboxylate (S1 -13), as described in patent application WO-A-95/07897.
S2) Compounds from the group of the 8-quinolinoxy derivatives (S2):
S2a) Compounds of the 8-quinolinoxyacetic acid type (S2a), preferably 1-methylhexyl (5-chloro-8quinolinoxy)acetate (cloquintocet-mexyl) (S2-1), 1,3-dimethylbut-l-yl (5-chloro-8quinolinoxy)acetate (S2-2), 4-allyloxybutyl (5-chloro-8-quinolinoxy)acetate (S2-3), 1allyloxyprop-2-yl (5-chloro-8-quinolinoxy)acetate (S2-4), ethyl (5-chloro-8-quinolinoxy)acetate (S2-5), methyl 5-chloro-8-quinolinoxyacetate (S2-6), allyl (5-chloro-8-quinolinoxy)acetate (S27), 2-(2-propylideneiminoxy)-l-ethyl (5-chloro-8-quinolinoxy)acetate (S2-8), 2-oxoprop-l-yl (5-chloro-8-quinolinoxy)acetate (S2-9) and related compounds, as described in EP-A-86750, EP-A-94349 and EP-A-191736 or EP-A-0 492 366, and also (5-chloro-8-quinolinoxy)acetic
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S2b) Compounds of the (5-chloro-8-quinolinoxy)malonic acid type (S2b), preferably compounds such as diethyl (5-chloro-8-quinolinoxy)malonate, diallyl (5-chloro-8-quinolinoxy)malonate, methyl ethyl (5-chloro-8-quinolinoxy)malonate and related compounds, as described in EP-A-0 582 198.
53) Active compounds of the dichloroacetamide type (S3), which are frequently used as preemergence safeners (soil-acting safeners), for example dichlormid (N,N-diallyl-2,2-dichloroacetamide) (S3-1),
R-29148 (3-dichloroacetyl-2,2,5-trimethyl-l,3-oxazolidine) from Stauffer (S3-2),
R-28725 (3-dichloroacetyl-2,2-dimethyl-1,3-oxazolidine) from Stauffer (S3-3), benoxacor (4-dichloroacetyl-3,4-dihydro-3-methyl-2H-l,4-benzoxazine) (S3-4),
PPG-1292 (N-allyl-N-[(l,3-dioxolan-2-yl)methyl]dichloroacetamide) from PPG Industries (S3-5),
DKA-24 (N-allyl-N-[(allylaminocarbonyl)methyl]dichloroacetamide) from Sagro-Chem (S36),
AD-67 or MON 4660 (3-dichloroacetyl-l-oxa-3-azaspiro[4.5]decane) fromNitrokemia or Monsanto (S3-7),
11-35 (1-dichloroacetylazepane) from TRI-Chemical RT (S3-8),
Diclonon (Dicyclonon) or BAS145138 or LAB145138 (S3-9) ((RS)-l-dichloroacetyl-3,3,8a-trimethylperhydropyrrolo[l,2-a]pyrimidin-6-one) from BASF, furilazole or MON 13900 ((RS)-3-dichloroacetyl-5-(2-furyl)-2,2-dimethyloxazolidine) (S310), and the (R) isomer thereof (S3-11).
54) Compounds from the class of the acylsulfonamides (S4):
S4a) N-Acylsulfonamides of the formula (S4a) and salts thereof, as described in WO-A-97/45016,
Figure AU2017379281A1_D0217
in which
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Ra1 is (Ci-C6)-alkyl, (C3-C6)-cycloalkyl, where the 2 latter radicals are substituted by Va substituents from the group of halogen, (Ci-C4)-alkoxy, (Ci-C6)-haloalkoxy and (C1-C4)alkylthio and, in the case of cyclic radicals, also by (Ci-C4)-alkyl and (Ci-C4)-haloalkyl;
Ra2 is halogen, (Ci-C4)-alkyl, (Ci-C4)-alkoxy, CF3;
mA is 1 or 2;
Va is 0, 1, 2 or 3;
S4b) Compounds of the 4-(benzoylsulfamoyl)benzamide type of the formula (S4b) and salts thereof, as described in WO-A-99/16744,
Figure AU2017379281A1_D0218
Figure AU2017379281A1_D0219
in which
Rb1, Rb2 are independently hydrogen, (Ci-C6)-alkyl, (C3-C6)-cycloalkyl, (C3-C6)-alkenyl, (C3Ce)-alkynyl,
Rb3 is halogen, (Ci-C4)-alkyl, (Ci-C4)-haloalkyl or (Ci-C4)-alkoxy and me is 1 or 2, for example those in which
Rb1 = cyclopropyl, Rb2 = hydrogen and (Rb3) = 2-OMe (cyprosulfamide, S4-1),
Rb1 = cyclopropyl, Rb2 = hydrogen and (Rb3) = 5-Cl-2-OMe (S4-2),
Rb1 = ethyl, Rb2 = hydrogen and (Rb3) = 2-OMe (S4-3),
Rb1 = isopropyl, Rb2 = hydrogen and (Rb3) = 5-Cl-2-OMe (S4-4) and
Rb1 = isopropyl, Rb2 = hydrogen and (Rb3) = 2-OMe (S4-5);
S4C) Compounds from the class of the benzoylsulfamoylphenylureas of the formula (S4C), as described m EP-A-365484,
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Figure AU2017379281A1_D0220
Figure AU2017379281A1_D0221
in which
Rc1, Rc2 are independently hydrogen, (Ci-Cs)-alkyl, (C3-Cs)-cycloalkyl, (C3-C6)-alkenyl, (C3-Ce)-alkynyl,
Rc3 is halogen, (Ci-C4)-alkyl, (Ci-C4)-alkoxy, CF3 and me is 1 or 2;
for example l-[4-(N-2-methoxybenzoylsulfamoyl)phenyl]-3-methylurea, l-[4-(N-2-methoxybenzoylsulfamoyl)phenyl]-3,3-dimethylurea, l-[4-(N-4,5-dimethylbenzoylsulfamoyl)phenyl]-3-methylurea;
S4d) Compounds of the N-phenylsulfonylterephthalamide type of the formula (S4d) and salts thereof, which are known, for example, from CN 101838227,
Figure AU2017379281A1_D0222
in which
Rd4 is halogen, (Ci-C4)-alkyl, (Ci-C4)-alkoxy, CF3;
idd is 1 or 2;
Rd5 is hydrogen, (Ci-Cej-alkyl, (C3-C6)-cycloalkyl, (C2-C6)-alkenyl, (C2-C6)-alkynyl or (C5Cej-cycloalkenyl.
S5) Active compounds from the class of the hydroxyaromatics and the aromatic-aliphatic carboxylic acid derivatives (S5), for example ethyl 3,4,5-triacetoxybenzoate, 3,5-dimethoxy-4hydroxybenzoic acid, 3,5-dihydroxybenzoic acid, 4-hydroxysalicylic acid, 4-fluorosalicyclic
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56) Active compounds from the class of the l,2-dihydroquinoxalin-2-ones (S6), for example 1methyl-3 -(2-thienyl)-1,2-dihydroquinoxalin-2-one, 1 -methyl-3-(2-thienyl)-1,2dihydroquinoxaline-2-thione, 1 -(2-aminoethyl)-3 -(2-thienyl)-1,2-dihydroquinoxalin-2-one hydrochloride, 1 -(2-methylsulfonylaminoethyl)-3-(2-thienyl)-1,2-dihydroquinoxalin-2-one, as described in WO-A-2005/112630.
57) Compounds from the class of the diphenylmethoxyacetic acid derivatives (S7), e.g. methyl diphenylmethoxyacetate (CAS Reg. No. 41858-19-9) (S7-1), ethyl diphenylmethoxyacetate or diphenylmethoxyacetic acid, as described in WO-A-98/38856.
58) Compounds of the formula (S8), as described in WO-A-98/27049,
Figure AU2017379281A1_D0223
Figure AU2017379281A1_D0224
Figure AU2017379281A1_D0225
(S8) in which the symbols and indices are defined as follows:
Rd1 is halogen, (Ci-CQ-alkyl, (Ci-CQ-haloalkyl, (Ci-CQ-alkoxy, (Ci-CQ-haloalkoxy,
Rd2 is hydrogen or (Ci-CQ-alkyl,
Rd3 is hydrogen, (Ci-Cs)-alkyl, (CT-CQ-alkcnyl, (Cz-CQ-alkynyl or aryl, where each of the aforementioned carbon-containing radicals is unsubstituted or substituted by one or more, preferably up to three identical or different radicals from the group consisting of halogen and alkoxy; or salts thereof, no is an integer from 0 to 2.
S9) active compounds from the class of the 3-(5-tetrazolylcarbonyl)-2-quinolones (S9), for example l,2-dihydro-4-hydroxy-l-ethyl-3-(5-tetrazolylcarbonyl)-2-quinolone (CAS Reg. No. 21947918-2), l,2-dihydro-4-hydroxy-l-methyl-3-(5-tetrazolylcarbonyl)-2-quinolone (CAS Reg. No. 95855-00-8), as described in WO-A-199/000020;
S10) Compounds of the formula (S10a) or (S10b) as described in WO-A-2007/023719 and WO-A-2007/023764
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Figure AU2017379281A1_D0226
Figure AU2017379281A1_D0227
Re1 is halogen, (Ci-C4)-alkyl, methoxy, nitro, cyano, CF3, OCF3
Ye, Ze are independently O or S,
nE is an integer from 0 to 4,
Re2 is (Ci-Ci6)-alkyl, (Cz-Cej-alkenyl, (C3-C6)-cycloalkyl, aryl; benzyl, halobenzyl,
Re3 is hydrogen or (Ci-Cej-alkyl.
SI 1) Active compounds of the oxyimino compound type (SI 1), which are known as seed-dressing agents, for example oxabetrinil ((Z)-l,3-dioxolan-2-ylmetiioxyimino(phenyl)acetonitrile) (SI 1-1), which is known as a seed-dressing safener for millet/sorghum against metolachlor damage, fluxofenim (l-(4-chlorophenyl)-2,2,2-trifluoro-l -ethanone 0-(1,3-dioxolan-2ylmethyl)oxime) (SI 1-2), which is known as a seed-dressing safener for millet/sorghum against metolachlor damage, and cyometrinil or CGA-43089 ((Z)-cyanometiioxyimino(phenyl)acetonitrile) (SI 1-3), which is known as a seed-dressing safener for millet/sorghum against metolachlor damage.
S12) active compounds from the class of the isotitiochromanones (S12), for example methyl [(3-oxolH-2-benzotitiopyran-4(3H)-ylidene)metiioxy]acetate (CAS Reg. No. 205121-04-6) (S12-1) and related compounds from WO-A-1998/13361.
S13) One or more compounds from group (SI3): naphthalic anhydride (1,8-naphthalenedicarboxylic anhydride) (S13-1), which is known as a seed-dressing safener for com against thiocarbamate herbicide damage,
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171 fenclorim (4,6-dichloro-2-phenylpyrimidine) (SI3-2), which is known as a safener for pretilachlor in sown rice, flurazole (benzyl 2-chloro-4-trifluorometiiyl-l,3-thiazole-5-carboxylate) (S13-3), which is known as a seed-dressing safener for millei/sorghum against alachlor and metolachlor damage,
CL 304415 (CAS Reg. No. 31541-57-8) (4-carboxy-3,4-dihydro-2H-l-benzopyran-4-acetic acid) (S13-4) from American Cyanamid, which is known as a safener for com against damage by imidazolinones,
MG 191 (CAS Reg. No. 96420-72-3) (2-dichloromethyl-2-methyl-l,3-dioxolane) (S13-5) from Nitrokemia, which is known as a safener for com,
MG 838 (CAS Reg. No. 133993-74-5) (2-propenyl l-oxa-4-azaspiro[4.5]decane-4-carbodithioate) (S13-6) fromNitrokemia disulfoton (0,0-diethyl S-2-ethylthioethyl phosphorodithioate) (SI3-7), dietholate (0,0-diethyl O-phenyl phosphorothioate) (SI3-8), mephenate (4-chlorophenyl methylcarbamate) (SI3-9).
514) active compounds which, in addition to herbicidal action against weeds, also have safener action on crop plants such as rice, for example dimepiperate or MY-93 (5-1 -methyl 1-phenylethylpiperidine-1-carbothioate), which is known as a safener for rice against damage by the herbicide molinate, daimuron or SK 23 (1-(1-methyl-l-phenylethy 1)-3-p-tolylurea), which is known as safener for rice against imazosulfuron herbicide damage, cumyluron = JC-940 (3-(2-chlorophenylmethyl)-1-(1 -methyl-1-phenylethyl)urea, see JP-A60087254), which is known as safener for rice against damage by some herbicides, methoxyphenone or NK 049 (3,3'-dimetiiyl-4-methoxybenzophenone), which is known as a safener for rice against damage by some herbicides, “CSB (1-bromo-4-(chloromethylsulfonyl)benzene) fromKumiai, (CAS Reg. No. 54091-06-4), which is known as a safener against damage by some herbicides in rice.
515) Compounds of the formula (S15) or tautomers thereof
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Figure AU2017379281A1_D0228
as described in WO-A-2008/131861 and WO-A-2008/131860 in which
Rh1 is a (Ci-Cej-haloalkyl radical and
Rh2 is hydrogen or halogen and
Rh3, Rh4 are each independently hydrogen, (Ci-Ci6)-alkyl, (C2-Ci6)-alkenyl or (C2-Ci6)-alkynyl, where each of the 3 latter radicals is unsubstituted or substituted by one or more radicals from the group of halogen, hydroxyl, cyano, (Ci-CQ-alkoxy, (Ci-CQ-haloalkoxy, (CiCQ-alkylthio, (Ci-CQ-alkylamino, di[(Ci-C4)-alkyl]amino, [(Ci-C4)-alkoxy]carbonyl, [(Ci-C4)-haloalkoxy]carbonyl, (C3-C6)-cycloalkyl which is unsubstituted or substituted, phenyl which is unsubstituted or substituted, and heterocyclyl which is unsubstituted or substituted, or (C3-C6)-cycloalkyl, (C4-C6)-cycloalkenyl, (C3-C6)-cycloalkyl fused on one side of the ring to a 4 to 6-membered saturated or unsaturated carbocyclic ring, or (C4-C6)-cycloalkenyl fused on one side of the ring to a 4 to 6-membered saturated or unsaturated carbocyclic ring, where each of the 4 latter radicals is unsubstituted or substituted by one or more radicals from the group of halogen, hydroxyl, cyano, (Ci-C4)alkyl, (Ci-C4)haloalkyl, (CiC4)alkoxy, (Ci-C4)haloalkoxy, (Ci-C4)alkylthio, (Ci-C4)alkylamino, di[(CiC4)alkyl]amino, [(Ci-C4)alkoxy]carbonyl, [(Ci-C4)haloalkoxy]carbonyl, (C3Gjcycloalkyl which is unsubstittrted or substituted, phenyl which is unsubstittrted or substituted, and heterocyclyl which is unsubstittrted or substituted, or
Rh3 is (Ci-C4)-alkoxy, (C2-C4)-alkenyloxy, (C2-C6)-alkynyloxy or (C2-C4)-haloalkoxy and
Rh4 is hydrogen or (Ci-C4)-alkyl or
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Rh3 and Rh4 together with the directly bonded nitrogen atom are a four- to eight-membered heterocyclic ring which, as well as the nitrogen atom, may also contain further ring heteroatoms, preferably up to two further ring heteroatoms from the group of N, O and S, and which is unsubstituted or substituted by one or more radicals from the group of halogen, cyano, nitro, (Ci-CQ-alkyl, (CiCQ-haloalkyl, (Ci-CQ-alkoxy, (Ci-CQ-haloalkoxy and (Ci-CQ-alkyltirio.
S16) Active compounds which are used primarily as herbicides but also have safener action on crop plants, for example (2,4-dichlorophenoxy)acetic acid (2,4-D), (4-chlorophenoxy)acetic acid, (R,S)-2-(4-chloro-o-tolyloxy)propionic acid (mecoprop),
4-(2,4-dichlorophenoxy)butyric acid (2,4-DB), (4-chloro-o-tolyloxy)acetic acid (MCPA),
4-(4-chloro-o-tolyloxy)butyric acid,
4-(4-chlorophenoxy)butyric acid,
3,6-dichloro-2-methoxybenzoic acid (dicamba),
-(ethoxycarbonyl)etiiyl 3,6-dichloro-2-methoxybenzoate (lactidichlor-ethyl).
Preferred safeners in combination with the compounds of the formula (I) according to the invention and/or salts thereof, in particular with the compounds of the formulae (1.1) to (1.116) and/or salts thereof, are: cloquintocet-mexyl, cyprosulfamide, fenchlorazole-ethyl, isoxadifen-ethyl, mefenpyr-diethyl, fenclorim, cumyluron, S4-1 and S4-5, and particularly preferred safeners are: cloquintocet-mexyl, cyprosulfamide, isoxadifen-ethyl and mefenpyr-diethyl.
Biological examples:
Experimental part 1
A.
Post-emergence herbicidal action and crop plant compatibility
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Seeds of monocotyledonous and dicotyledonous weeds and crop plants were placed in sandy loam in plastic or wood-fiber pots, covered with soil and cultivated in a greenhouse under controlled growth conditions. 2 to 3 weeks after sowing, the test plants were treated at the one-leaf stage. The compounds of the invention, formulated in the form of wettable powders (WP) or as emulsion concentrates (EC), were then sprayed onto the green parts of the plants as aqueous suspension or emulsion with addition of 0.5% additive at a water application rate of 600 1/ha (converted). After the test plants had been kept in the greenhouse under optimum growth conditions for about 3 weeks, the activity of the preparations was rated visually in comparison to untreated controls. For example, 100% activity = the plants have died, 0% activity = like control plants.
Tables Al to Al 4 below show the effects of selected compounds of the general formula (I) according to Tables El to 1.116 on various harmful plants and an application rate corresponding to 1280 g/ha or 320 g/ha, which were obtained by the experimental procedure mentioned above.
Table Al
Compound Example No. Alopecurus myosuroides Application rate [g/ha]
1.1-162 100 1280
1.1-162 90 320
1.3-162 100 1280
1.3-162 100 320
1.5-162 100 1280
1.5-162 90 320
1.11-162 100 320
Table A2
Compound Example No. Echinochloa crus-galli Application rate [g/ha]
1.1-162 100 1280
1.1-162 100 320
1.3-162 100 1280
1.3-162 90 320
1.5-162 100 1280
1.11-162 90 320
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Table A3
Compound Example No. Setaria viridis Application rate [g/ha]
1.1-162 100 1280
1.1-162 100 320
1.3-162 100 1280
1.3-162 100 320
1.5-162 100 1280
1.5-162 100 320
1.11-162 100 320
1.12-451 100 1280
1.12-451 100 320
Table A4
Compound Example No. Abutilon theophrasti Application rate [g/ha]
1.1-162 100 1280
1.1-162 100 320
1.3-162 100 1280
1.3-162 100 320
1.5-162 100 1280
1.5-162 100 320
1.11-162 100 320
1.12-451 100 1280
1.12-451 100 320
Table A5
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Compound Example No. Amaranthus retroflexus Application rate [g/ha]
1.1-162 100 1280
1.1-162 100 320
1.3-162 100 1280
1.3-162 90 320
1.5-162 100 1280
Lll-162 100 320
1.12-451 100 1280
1.12-451 100 320
Table A6
Compound Example No. Matricaria inodora Application rate [g/ha]
1.1-162 100 1280
1.1-162 100 320
1.3-162 100 1280
1.3-162 100 320
1.5-162 100 1280
Lll-162 100 320
1.12-451 100 1280
1.12-451 90 320
Table A7
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Compound Example No. Polygonum convolvulus Application rate [g/ha]
1.1-162 100 1280
1.1-162 100 320
1.3-162 100 1280
1.3-162 100 320
1.5-162 100 1280
1.5-162 100 320
1.11-162 100 320
1.12-451 100 1280
1.12-451 100 320
Table A8
Compound Example No. Stellaria media Application rate [g/ha]
1.1-162 100 1280
1.1-162 100 320
1.3-162 100 1280
1.3-162 100 320
1.5-162 100 1280
1.5-162 100 320
1.11-162 100 320
1.12-451 100 1280
1.12-451 100 320
Table A9
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Compound Example No. Viola tricolor Application rate [g/ha]
1.1-162 100 1280
1.1-162 100 320
1.3-162 100 1280
1.3-162 100 320
1.5-162 100 1280
1.5-162 100 320
1.11-162 100 320
1.12-451 100 1280
1.12-451 100 320
Table Al0
Compound Example No. Veronica persica Application rate [g/ha]
1.1-162 100 1280
1.3-162 100 1280
1.5-162 100 1280
1.11-162 100 320
1.12-451 100 1280
Table All
Compound Example No. Hordeum murinum Application rate [g/ha]
1.1-162 100 1280
1.3-162 100 1280
1.5-162 100 1280
Table A12
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Compound Example No. Lolium rigidum Application rate [g/ha]
1.3-162 90 1280
1.5-162 90 1280
Table Al3
Compound Example No. Avena fatua Application rate [g/ha]
1.1-162 100 1280
1.1-162 90 320
1.3-162 90 1280
1.3-162 90 320
1.5-162 100 1280
Table A14
Compound Example No. Ipomoea purpurea Application rate [g/ha]
1.1-162 100 1280
1.1-162 100 320
1.3-162 90 1280
1.5-162 90 1280
1.11-162 90 320
1.12-451 100 1280
1.12-451 100 320
As demonstrated by the results, the compounds according to the invention of the general formula (I) have, in post-emergence applications, good herbicidal activity on harmful plants such as Alopecurus myorsuroides, Echinochloa crus-galli, Setaria viridis, Abutilon theophrasti, Amaranthus retroflexus, Matricaria inodora, Polygonum convolvulus, Stellaria media, Viola tricolor, Veronica persica, Hordeum 10 murinum, Lolium rigidum, Avena fatua and Ipomoea purpurea at an application rate of 1.28 kg of active substance or less per hectare. At the same time, some of the compounds according to the invention leave Gramineae crops such as barley, wheat, rye, millet/sorghum, com, rice or sugar cane, virtually undamaged when applied post-emergence, even at high active compound dosages. In addition, some
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B. Pre-emergence herbicidal action and crop plant compatibility
Seeds of monocotyledonous and dicotyledonous weed plants and crop plants were placed in plastic or organic planting pots and covered with soil. The compounds of the invention, formulated in the form of wettable powders (WP) or as emulsion concentrates (EC), were then applied onto the surface of the covering soil as aqueous suspension or emulsion with addition of 0.5% additive at a water application rate of 600 1/ha (converted). After the treatment, the pots were placed in a greenhouse and kept under good growth conditions for the test plants. After about 3 weeks, the effect of the preparations was scored visually in comparison with untreated controls as percentages. For example, 100% activity = the plants have died, 0% activity = like control plants.
Tables Bl to B14 below show the effects of selected compounds of the general formula (I) according to Tables 1.1 to 1.116 on various harmful plants and an application rate corresponding to 1280 g/ha or 320 g/ha, which were obtained by the experimental procedure mentioned above.
Table Bl
Compound Example No. Alopecurus myosuroides Application rate [g/ha]
1.1-162 100 1280
1.1-162 90 320
1.3-162 90 1280
1.3-162 90 320
1.5-162 90 1280
1.5-162 90 320
1.11-162 100 320
1.12-451 90 1280
Table B2
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Compound Example No. Echinochloa crus-galli Application rate [g/ha]
1.1-162 100 1280
1.3-162 100 1280
1.5-162 100 1280
1.11-162 100 320
Table B3
Compound Example No. Setaria viridis Application rate [g/ha]
1.1-162 100 1280
1.1-162 100 320
1.3-162 100 1280
1.3-162 100 320
1.5-162 100 1280
1.5-162 100 320
1.11-162 100 320
1.12-451 100 1280
1.12-451 90 320
Table B4
Compound Example No. Abutilon theophrasti Application rate [g/ha]
1.1-162 100 1280
1.1-162 100 320
1.3-162 100 1280
1.3-162 100 320
1.5-162 100 1280
1.5-162 100 320
1.11-162 100 320
1.12-451 100 1280
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Table B5
Compound Example No. Amaranthus retroflexus Application rate [g/ha]
1.1-162 100 1280
1.1-162 100 320
1.3-162 100 1280
1.3-162 100 320
1.3-290 90 1280
1.5-162 100 1280
1.5-162 100 320
1.11-162 100 320
1.12-451 100 1280
1.12-451 100 320
Table B6
Compound Example No. Matricaria inodora Application rate [g/ha]
1.1-162 100 1280
1.1-162 100 320
1.3-162 100 1280
1.3-162 100 320
1.5-162 100 1280
1.5-162 100 320
1.11-162 100 320
1.12-451 90 1280
Table B7
Compound Example No. Polygonum convolvulus Application rate [g/ha]
1.1-162 100 1280
1.1-162 100 320
1.3-162 100 1280
1.3-162 100 320
1.5-162 100 1280
1.5-162 100 320
1.11-162 100 320
1.12-451 100 1280
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Table B8
Compound Example No. Stellaria media Application rate [g/ha]
1.1-162 100 1280
1.1-162 100 320
1.3-162 100 1280
1.3-162 90 320
1.5-162 100 1280
1.5-162 100 320
1.11-162 100 320
1.12-451 100 1280
1.12-451 100 320
Table B9
Compound Example No. Viola tricolor Application rate [g/ha]
1.1-162 100 1280
1.1-162 100 320
1.3-162 100 1280
1.3-162 100 320
1.5-162 100 1280
1.5-162 100 320
1.11-162 100 320
1.12-451 100 1280
1.12-451 100 320
Table BIO
Compound Example No. Veronica persica Application rate [g/ha]
1.1-162 100 1280
1.3-162 100 1280
1.5-162 100 1280
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Table Bl 1
Compound Example No. Hordeum murinum Application rate [g/ha]
1.1-162 100 1280
1.1-162 90 320
1.3-162 100 1280
1.3-162 90 320
1.5-162 100 1280
Table B12
Compound Example No. Lolium rigidum Application rate [g/ha]
1.1-162 100 1280
1.3-162 90 1280
1.5-162 90 1280
1.11-162 90 1280
Table B13
Compound Example No. Avena faiua Application rate [g/ha]
1.1-162 100 1280
1.1-162 90 320
1.3-162 90 1280
1.3-162 90 320
1.5-162 90 1280
1.5-162 90 320
1.11-162 90 320
1.12-451 90 1280
Table B14
Compound Example No. Ipomoea purpurea Application rate [g/ha]
1.1-162 100 1280
1.3-162 90 1280
1.5-162 90 1280
1.11-162 90 320
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As demonstrated by the results, the compounds according to the invention of the general formula (1) have, in pre-emergence applications, good herbicidal activity on harmful plants, for example harmful plants such as Alopecurus myosuroides, Echinochloa crus-galli, Setaria viridis, Abutilon theophrasti, Amaranthus retroflexus, Matricaria inodora, Polygonum convolvolus, Stellaria media, Viola tricolor, Veronica persica, Hordeum murinum, Lolium rigidum, Avena fatua, Ipomoea purpurea at an application rate of 1.28 kg of active substance or less per hectare. At the same time, some of the compounds according to the invention leave Gramineae crops such as barley, wheat, rye, millet/sorghum, com, rice or sugar cane, virtually undamaged when applied pre-emergence, even at high active compound dosages. In addition, some substances are also harmless to dicotyledonous crops such as soya, cotton, oilseed rape or sugar beet.
Some of the compounds according to the invention exhibit high selectivity and are therefore suitable for controlling unwanted vegetation in agricultural crops by the pre-emergence method.
Experimental part 2
C. Herbicidal post-emergence action
Seeds of mono- and dicotyledonous weed plants were placed in plastic pots in sandy loam soil (doubly sown with in each case one species of mono- or dicotyledonous weed plants per pot), covered with soil and cultivated in a greenhouse under controlled growth conditions. 2 to 3 weeks after sowing, the test plants were treated at the one-leaf stage. The compounds of the invention, formulated in the form of wettable powders (WP) or as emulsion concentrates (EC), were applied onto the green parts of the plants as aqueous suspension or emulsion with addition of 0.5% additive at a water application rate of 600 liters per hectare (converted). After the test plants had been kept in the greenhouse under optimum growth conditions for about 3 weeks, the activity of the preparations was rated visually in comparison to untreated controls. For example, 100% activity = the plants have died, 0% activity = like control plants.
Tables Cl to C8 below show the effects of selected compounds of the general formula (I) according to Tables 1.1 to 1.116 on various harmful plants and an application rate corresponding to 1280 g/ha or 320 g/ha, which were obtained by the experimental procedure mentioned above.
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Table Cl
Compound Example No. Echinochloa crus-galli Application rate [g/ha]
1.1-177 100 1280
1.1-300 100 1280
1.1-451 100 1280
1.2-162 100 320
1.2-177 100 320
1.2-290 100 1280
1.6-290 100 1280
Table C2
Compound Example No. Lolium rigidum Application rate [g/ha]
1.2-162 90 320
1.2-177 90 320
1.2-290 100 1280
1.6-290 90 1280
Table C3
Compound Example No. Poa Annua Application rate [g/ha]
1.1-177 100 1280
1.1-300 100 320
1.1-451 100 320
1.2-162 100 320
1.2-177 100 320
1.2-290 100 320
1.3-290 100 1280
1.3-451 100 320
1.5-451 100 1280
1.6-290 100 320
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Table C4
Compound Example No. Setaria viridis Application rate [g/ha]
1.1-91 100 1280
1.1-177 100 1280
1.1-300 100 320
1.2-162 100 320
1.2-290 100 320
1.2-300 90 1280
1.5-451 90 1280
1.6-290 100 320
Table C5
Compound Example No. Abutilon theophrasti Application rate [g/ha]
1.1-91 100 1280
1.1-177 100 1280
1.1-289 100 1280
1.1-290 100 320
1.1-300 100 320
1.1-451 100 320
1.2-162 100 320
1.2-177 100 320
1.2-290 100 320
1.2-300 100 1280
1.3-290 100 1280
1.3-451 100 320
1.5-290 100 1280
1.5-451 100 320
1.6-290 100 320
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Table C6
Compound Example No. Amaranthus retroflexus Application rate [g/ha]
1.1-72 100 320
1.1-91 100 320
1.1-177 100 1280
1.1-289 100 320
1.1-300 100 320
1.1-451 100 1280
1.2-162 100 320
1.2-177 100 320
1.2-290 100 320
1.2-300 100 320
1.3-451 100 1280
1.6-290 100 320
Table C7
Compound Example No. Matricaria inodora Application rate [g/ha]
1.1-72 100 1280
1.1-91 100 1280
1.1-177 100 320
1.1-289 100 1280
1.1-290 100 1280
1.1-300 100 320
1.1-451 90 320
1.2-162 100 320
1.2-177 100 320
1.2-290 100 320
1.3-290 90 1280
1.3-451 90 320
1.5-290 100 1280
1.5-451 90 1280
1.6-290 100 320
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Table C8
Compound Example No. Stellaria media Application rate [g/ha]
1.1-91 100 1280
1.1-177 100 320
1.1-290 100 1280
1.1-300 100 320
1.1-451 100 320
1.2-162 100 320
1.2-177 100 320
1.2-290 100 320
1.2-300 100 1280
1.3-451 100 320
1.5-290 100 1280
1.5-451 100 1280
1.6-290 100 320
As the results show, compounds of the general formula (1) according to the invention, in post-emergence applications, have very good herbicidal activity against harmful plants. For example, compounds of the general formula (1), applied post-emergence, have very good herbicidal activity (80% to 100% herbicidal activity) against harmful plants such as Abutilon theophrasti, Amaranthus retrqflexus, Echinochloa crus-galli, Lolium rigidum, Matricaria inodora, Poa annua, Setaria viridis and Stellaria media at an application rate of 1280 g or 320 g of active substance or less per hectare.
D. Herbicidal pre-emergence action
Seeds of mono- and dicotyledonous weed plants were placed in plastic pots in sandy loam soil (doubly sown with in each case one species of mono- or dicotyledonous weed plants per pot) and covered with soil. The compounds of the invention, formulated in the form of wettable powders (WP) or as emulsion concentrates (EC), were then applied onto the surface of the covering soil as aqueous suspension or emulsion with addition of 0.5% additive at a water application rate of 600 liters per hectare (converted). After the treatment, the pots are placed in a greenhouse and kept under good growth conditions for the trial plants. After about 3 weeks, the effect of the preparations was scored visually in comparison with untreated controls as percentages. For example, 100% activity = the plants have died, 0% activity = like control plants.
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Tables DI to D8 below show the effects of selected compounds of the general formula (I) according to Tables 1.1 to 1.116 on various harmful plants and an application rate corresponding to 1280 g/ha or 320 g/ha, which were obtained by the experimental procedure mentioned above.
Table DI
Compound Example No. Echinochloa crus-galli Application rate [g/ha]
1.1-177 100 1280
1.1-300 100 320
1.2-162 100 320
1.2-177 100 320
1.2-290 100 320
1.6-290 90 320
Table D2
Compound Example No. Lolium rigidum Application rate [g/ha]
1.1-177 90 320
1.1-300 90 1280
1.2-162 90 320
1.2-177 90 320
1.2-290 100 1280
1.3-451 90 1280
1.5-290 90 1280
1.5-451 90 1280
1.6-290 90 320
Table D3
Compound Example No. Poa Annua Application rate [g/ha]
1.1-177 100 1280
1.1-289 100 1280
1.1-290 90 320
1.1-300 90 320
1.1-451 90 1280
1.2-162 100 320
1.2-177 100 320
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Compound Example No. Poa Annua Application rate [g/ha]
1.2-290 100 320
1.2-300 90 1280
1.3-290 90 1280
1.3-451 90 320
1.5-290 90 320
1.5-451 100 320
1.6-290 100 320
Table D4
Compound Example No. Setaria viridis Application rate [g/ha]
1.1-177 100 320
1.1-289 90 1280
1.1-290 90 1280
1.1-300 100 1280
1.1-451 100 1280
1.2-162 100 320
1.2-177 100 320
1.2-290 100 1280
1.2-300 90 320
1.3-290 90 1280
1.3-451 100 1280
1.5-290 90 1280
1.5-451 100 320
1.6-290 90 320
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Table D5
Compound Example No. Abutilon iheophrasti Application rate [g/ha]
1.1-91 100 1280
1.1-177 100 320
1.1-289 100 1280
1.1-290 90 1280
1.1-300 100 320
1.2-162 100 320
1.2-177 100 320
1.2-290 100 320
1.2-300 90 320
1.3-290 100 1280
1.5-290 100 1280
1.6-290 100 320
Table D6
Compound Example No. Amaranihus retroflexus Application rate [g/ha]
1.1-72 90 1280
1.1-91 100 320
1.1-177 90 1280
1.1-289 90 1280
1.1-290 100 1280
1.1-300 90 1280
1.1-451 90 1280
1.2-162 100 320
1.2-177 90 320
1.2-290 100 320
1.2-300 100 320
1.3-290 90 1280
1.6-290 100 320
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Table D7
Compound Example No. Matricaria inodora Application rate [g/ha]
1.1-91 90 1280
1.1-177 100 1280
1.1-289 100 1280
1.1-290 100 320
1.1-300 100 320
1.1-451 100 1280
1.2-162 100 320
1.2-177 100 320
1.2-290 100 320
1.2-300 90 1280
1.3-290 100 1280
1.5-290 100 320
1.5-451 90 1280
1.6-290 100 320
Table D8
Compound Example No. Stellaria media Application rate [g/ha]
1.1-72 90 1280
1.1-177 100 1280
1.1-289 100 1280
1.1-290 100 320
1.1-300 100 320
1.1-451 100 320
1.2-162 100 320
1.2-177 100 320
1.2-290 100 320
1.2-300 90 320
1.3-290 100 1280
1.3-451 100 320
1.5-290 100 320
1.5-451 100 1280
1.6-290 100 320
As the results show, compounds of the general formula (I) according to the invention, in pre-emergence applications, have very good herbicidal activity against harmful plants. For example, compounds of the general formula (I), applied pre-emergence, have very good activity (80% to 100% herbicidal activity)
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Experimental part 3
Measurement of the PS II activity in thylakoid membranes
Cooled fresh spinach leaves were comminuted and homogenized in 50 mM phosphate buffer, pH 6.8. 10 mM KC1, 0.34 M sucrose (sucrose buffer) (blender, 1 g of plant material/ml). The homogenate was subsequently filtered through 4 layers of Miracloth and the chloroplasts were isolated by centrifugation, i.e. 10 min of centrifugation at 4400 x g (4°C). The sediment was suspended in 25 ml of sucrose buffer and re-centrifuged for 10 min at 4400 x g (4°C). The sediment was then suspended in 40 ml of 50 mM phosphate buffer, pH 6.8, 10 mM KC1, without sucrose. In this step, the chloroplasts were osmotically ruptured and the thylakoid membranes were then obtained by centrifugation (10 min, 4400 x g, 4°C). The membrane sediment was finally suspended in about 20 ml of 50 mM phosphate buffer, pH 6.8, 10 mM KC1. Following protein determination and activity determination, the membrane suspension was divided into aliquots and frozen in liquid nitrogen. The aliquots were stored at -80°C. Under these conditions, the photosystem II preparation was storage stable for at least three months. The activity determination of photosystem II (PS II) was then carried out using the following test principle: The electron transfer from PS II to an artificial electron acceptor, 2,6-dichlorophenolindophenol (DCPIP), was measured with exposure to light. The concentration of the blue oxidized form of DCPIP was determined spectrophotometrically at wavelength λ = 595 nm. The enzyme-catalyzed reduction of DCPIP resulted in a colorless leuco form and thus in a decrease of the absorption at 595 nm in the reaction batch, which decrease was measured as a function of time. The activity determination was carried out in microtiter plates (96 cavities) in a reaction volume of 200 μΐ. Here, 155 μΐ of dilute membrane suspension were initially charged in 50 mM of phosphate buffer, pH 6.8, 10 mM KC1. Depending on the activity of the PS II preparation, the dilution was adjusted such that the measurement of the decrease in absorption (λ = 595 nm) was linear for at least 10 min. In each case 5 μΐ solution of the test compounds of a concentration of 100 μΜ in DMSO were added to the enzyme suspension; controls contained 5 μΐ DMSO; the final concentration of DMSO in the reaction batch was thus 2.5% (v/v); this concentration had no adverse effect on the enzymatic activity. On each microtiter plate, a known PS II inhibitor, for example metribuzin, was used as standard, which allowed the quality of the PS II test to be assessed. The reaction was started by addition of 40 μΐ DCPIP solution (600 μΜ in distilled water); the final concentration of DCPIP was 120 μΜ. Measurement of absorption was carried out over a period of 10 min at 22°C and with exposure to light. Using metribuzin as comparative substance, the results for the efficacy of the compounds of the general formula (I) at 100 μΜ are stated
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Effects of selected compounds of the general formula (I) according to the following table El:
Table El
No. Substance Effect
1 metribuzin ++++
2 1.1-72 ++++
3 1.1-86 ++++
4 1.1-162 ++++
5 1.1-177 ++++
6 1.1-290 ++++
7 1.1-300 +++
8 1.1-315 ++++
9 1.1-449 ++++
10 1.1-451 ++++
11 1.1-697 ++++
12 1.2-72 ++
13 1.2-86 ++++
14 1.2-162 ++++
15 1.2-177 ++++
16 1.2-290 ++++
17 1.2-300 ++++
18 1.3-451 +++
19 1.5-162 +++
20 1.25-162 ++++
Similar results were also achievable with further compounds of the general formula (I).
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Claims (9)

  1. Claims:
    1. A substituted heteroarylpyrrolone of the general formula (1) or salts thereof
    5 in which
    Q represents the moieties Q-1 to Q-29
    Q-21 Q-22 Q-23 Q-25 y— n 4/ X 5 N—N '„5 .N '('Ίτ' N—N 5/ O' 5/ >7 R R R R R R Q-26 Q-27 Q-28 Q-29
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    A1, A2, A3, A4 are identical or different and independently of one another represent N (nitrogen) or the moiety C-R8, but there are never more than two adjacent nitrogen atoms, and where R8 in the moiety C-R8 in each case has identical or different meanings according to the definition below,
    X and Y independently of one another represent C-H or the moiety C-R1, where
    X represents C-H if Y represents the moiety C-R1 and
    X represents the moiety C-R1 if Y represents C-H,
    R1 represents halogen, (Ci-Cs)-alkyl, (Ci-Cs)-haloalkyl, (Ci-Cs)-hydroxyalkyl, (Ci-Cs)alkoxyalkyl, (Ci-Cs)-alkoxy, (Ci-Cs)-haloalkoxy, (Ci-Cs)-alkylthio, (Ci-Cs)haloalkylthio, aryl, heteroaryl, aryloxy, heteroaryloxy, heterocyclyl, (C3-Cio)-cycloalkyl, (C3-Cio)-cycloalkyl-(Ci-Cs)-alkyl, (C3-C8)-halocycloalkyl, (C3-C8)-halocycloalkyl-(CiC8)-alkyl, (Ci-Cs)-alkylcarbonyl, (C2-C8)-alkenyl, (C2-C8)-alkynyl, tris-[(Ci-C8)alkyl]silyl-(C2-Cs)-alkynyl, NR10Rn,
    R3 represents hydroxy, hydrothio, halogen, NR10Rn, (Ci-Cs)-alkoxy, (C3-Cio)-cycloalkyl(Ci-Cs)-alkoxy, aryl-(Ci-C8)-alkoxy, (Ci-C8)-alkoxy-(Ci-C8)-alkoxy, arylcarbonyloxy, (Ci-Cs)-alkylcarbonyloxy, aryl-(Ci-C8)-alkylcarbonyloxy, heteroarylcarbonyloxy, (C3Cio)-cycloalkylcarbonyloxy, heterocyclylcarbonyloxy, (Ci-Cs)-haloalkylcarbonyloxy, (C2-C8)-alkenylcarbonyloxy, OC(O)OR12, OC(O)SR12, OC(S)OR12, OC(S)SR12, OSO2R13, OSO2OR12, OCHO,
    R4 and R7 independently of one another represent hydrogen, hydrothio, hydroxy, halogen, (CiC8)-alkyl, (Ci-C8)-haloalkyl, (C3-Cio)-cycloalkyl, (C3-Cio)-cycloalkyl-(Ci-C8)-alkyl, aryl, heteroaryl, heterocyclyl, aryl-(Ci-C8)-alkyl, heteroaryl-(Ci-C8)-alkyl, heterocyclyl(Ci-C8)-alkyl, (C2-C8)-alkenyl, (C2-C8)-alkynyl, (C2-C8)-haloalkenyl, (C2-C8)haloalkynyl, (C3-Cio)-halocycloalkyl, (C4-Cio)-cycloalkenyl, (C4-Cio)-halocycloalkenyl, aryl-(C2-C8)-alkenyl, heteroaryl-(C2-C8)-alkenyl, heterocyclyl-(C2-C8)-alkenyl, aryl-(C2C8)-alkynyl, heteroaryl-(C2-C8)-alkynyl, heterocyclyl-(C2-C8)-alkynyl, (C3-C10)cycloalkyl-(C2-C8)-alkynyl, arylcarbonyl-(Ci-C8)-alkyl, (Ci-C8)-alkylcarbonyl-(Ci-C8)alkyl, heteroarylcarbonyl-(Ci-C8)-alkyl, (C3-Cio)-cycloalkylcarbonyl-(Ci-C8)-alkyl, aryl(Ci-C8)-alkoxycarbonyl-(Ci-C8)-alkyl, (Ci-C8)-alkoxycarbonyl-(Ci-C8)-alkyl, (Ci-C8)alkoxy-(Ci-C8)-alkyl, arylcarbonyloxy-(Ci-C8)-alkyl, heteroarylcarbonyloxy-(Ci-C8)alkyl, heterocyclylcarbonyloxy-(Ci-C8)-alkyl, (Ci-C8)-alkylcarbonyloxy-(Ci-C8)-alkyl, (C3-C8)-cycloalkylcarbonyloxy-(Ci-C8)-alkyl, (Ci-C8)-haloalkoxy-(Ci-C8)-alkyl, aryl(Ci-C8)-alkoxy-(Ci-C8)-alkyl, heteroaryl-(Ci-C8)-alkoxy-(Ci-C8)-alkyl, CHO, C(O)R12,
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    C(O)OR12, C(O)NR10Rn, OR12, SR13, SOR13, SO2R13, NR10Rn, R10RnN-(Ci-C8)-alkyl, cyano-(Ci-C8)-alkyl, hydroxycarbonyl-(Ci-C8)-alkyl, hydroxycarbonyl, (Ci-C8)haloalkoxy-(Ci-C8)-alkylthio, (Ci-C8)-alkylthio-(Ci-C8)-alkylene, (Ci-C8)-haloalkylthio(Ci-C8)-alkylthio, (Ci-C8)-alkylthio-(Ci-C8)-alkylthio, aminocarbonyl, aminocarbonyl(Ci-C8)-alkyl, (Ci-C8)-alkylaminocarbonyl-(Ci-C8)-alkyl, (C3-C8)cycloalkylaminocarbonyl-(Ci-C8)-alkyl, (C2-C8)-alkenyloxycarbonyl-(Ci-C8)-alkyl, (C3C8)-cycloalkyl-(Ci-C8)-alkoxycarbonyl-Ci-C8)-alkyl, cyano, hydroxy-(Ci-C8)-alkyl, (C2C8)-alkenyloxy-(C 1 -C8)-alkyl, or where R4 and R7 together with the carbon atom to which they are respectively attached form a partially saturated ring having a total of 3 to 7 members which is optionally interrupted by one to three heteroatoms from the group consisting of N, O and S and optionally substituted further, if Q represents Q-3, Q-4, Q-8, Q-9, Q-12 or Q19,
    R5 represents hydrogen, formyl, (Ci-C8)-alkyl, (Ci-C8)-haloalkyl, hydroxy-(Ci-C8)-alkyl, hydroxycarbonyl-(Ci-C8)-alkyl, (Ci-C8)-alkoxy-(Ci-C8)-alkyl, (C3-Cio)-cycloalkyl, (C3Cw)-halocycloalkyl, aryl, heteroaryl, (C3-Cio)-cycloalkyl-(Ci-C8)-alkyl, heterocyclyl, (C2-C8)-alkenyl, (C2-C8)-alkynyl, NR10RH, aryl-(Ci-C8)-alkyl, heteroaryl-(Ci-C8)-alkyl, heterocyclyl-(Ci-C8)-alkyl, (Ci-C8)-cyanoalkyl, C(O)R12, C(O)OR12, C(O)NR10Rn, SO2R13, (Ci-C8)-alkoxycarbonyl-(Ci-C8)-alkyl, (C2-C8)-alkenyloxycarbonyl-(Ci-C8)alkyl, aryl-(Ci-C8)-alkoxycarbonyl-(Ci-C8)-alkyl, heteroaryl-(Ci-C8)-alkoxycarbonyl(Ci-C8)-alkyl, aryloxycarbonyl-(Ci-C8)-alkyl, arylcarbonyl-(Ci-C8)-alkyl, (Ci-C8)alkylcarbonyl-(Ci-C8)-alkyl, heteroarylcarbonyl-(Ci-C8)-alkyl, heterocyclylcarbonyl(Ci-C8)-alkyl, or where R4 and R5 together with the nitrogen atom or carbon atom to which they are respectively attached form a partially saturated ring having a total of 3 to 7 members which is optionally interrupted by one to three heteroatoms from the group consisting of N, O and S and optionally substituted further, if Q represents Q-13, Q-14 or Q-15,
    R6 represents hydrogen or (Ci-C8)-alkyl,
    R8 represents hydrogen, halogen, cyano, nitro, hydrothio, hydroxy, NR10RH, OR12, SR13, SOR13, SO2R13, thiocyanate, isothiocyanate, formyl, (Ci-C8)-alkyl, (C2-C8)-alkenyl, (C2C8)-alkynyl, (Ci-Cio)-haloalkyl, (C2-C8)-haloalkenyl, (C2-C8)-haloalkynyl, (C3-C10)cycloalkyl, (C3-Cio)-halocycloalkyl, (C4-Cio)-cycloalkenyl, (C4-Cio)-halocycloalkenyl,
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    R10 and R11 are identical or different and independently of one another represent hydrogen, (CiC8)-alkyl, (C2-C8)-alkenyl, (C2-C8)-alkynyl, (Ci-C8)-cyanoalkyl, (Ci-Cio)-haloalkyl, (C2C8)-haloalkenyl, (C2-C8)-haloalkynyl, (C3-Cio)-cycloalkyl, (C3-Cio)-halocycloalkyl, (C4Cio)-cycloalkenyl, (C4-Cio)-halocycloalkenyl, (Ci-C8)-alkoxy-(Ci-C8)-alkyl, (Ci-Cs)haloalkoxy-(Ci-C8)-alkyl, (Ci-C8)-alkyltitio-(Ci-C8)-alkyl, (Ci-C8)-haloalkyltitio-(CiC8)-alkyl, (Ci-C8)-alkoxy-(Ci-C8)-haloalkyl, aryl, aryl-(Ci-C8)-alkyl, heteroaryl, heteroaryl-(Ci-C8)-alkyl, (C3-Cio)-cycloalkyl-(Ci-C8)-alkyl, (C4-Cio)-cycloalkenyl-(CiWO 2018/114596
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    C8)-alkyl, COR12, SO2R13, (Ci-C8)-alkyl-HNO2S-, (C3-Cio)-cyeloalkyl-HN02S-, heterocyclyl, (Ci-C8)-alkoxycarbonyl-(Ci-C8)-alkyl, (Ci-C8)-alkoxycarbonyl, aryl-(CiC8)-alkoxycarbonyl-(Ci-C8)-alkyl, aryl-(Ci-C8)-alkoxycarbonyl, heteroaryl-(Ci-C8)alkoxycarbonyl, (C2-C8)-alkenyloxycarbonyl, (C2-C8)-alkynyloxycarbonyl, heterocyclyl(Ci-C8)-alkyl,
    R12 represents (Ci-C8)-alkyl, (C2-C8)-alkenyl, (C2-C8)-alkynyl, (Ci-C8)-cyanoalkyl, (Ci-Cio)haloalkyl, (C2-C8)-haloalkenyl, (C2-C8)-haloalkynyl, (C3-Cio)-cycloalkyl, (C3-C10)halocycloalkyl, (C4-Cio)-cycloalkenyl, (C4-Cio)-halocycloalkenyl, (Ci-C8)-alkoxy-(CiC8)-alkyl, (Ci-C8)-alkoxy-(Ci-C8)-haloalkyl, aryl, aryl-(Ci-C8)-alkyl, heteroaryl, heteroaryl-(Ci-C8)-alkyl, (C3-Cio)-cycloalkyl-(Ci-C8)-alkyl, (C4-Cio)-cycloalkenyl-(CiC8)-alkyl, (Ci-C8)-alkoxycarbonyl-(Ci-C8)-alkyl, (C2-C8)-alkenyloxycarbonyl-(Ci-C8)alkyl, aryl-(Ci-C8)-alkoxycarbonyl-(Ci-C8)-alkyl, hydroxycarbonyl-(Ci-C8)-alkyl, heterocyclyl, heterocyclyl-(Ci-C8)-alkyl,
    R13 represents (Ci-C8)-alkyl, (C2-C8)-alkenyl, (C2-C8)-alkynyl, (Ci-C8)-cyanoalkyl, (C1-C10)haloalkyl, (C2-C8)-haloalkenyl, (C2-C8)-haloalkynyl, (C3-Cio)-cycloalkyl, (C3-C10)halocycloalkyl, (C4-Cio)-cycloalkenyl, (C4-Cio)-halocycloalkenyl, (Ci-C8)-alkoxy-(CiC8)-alkyl, (Ci-C8)-alkoxy-(Ci-C8)-haloalkyl, aryl, aryl-(Ci-C8)-alkyl, heteroaryl, heteroaryl-(Ci-C8)-alkyl, heterocyclyl-(Ci-C8)-alkyl, (C3-Cio)-cycloalkyl-(Ci-C8)-alkyl, (C4-Cio)-cycloalkenyl-(Ci-C8)-alkyl, NR’R, and
    W represents oxygen or sulfur, where the cyclic structural elements of the radicals mentioned in R1, R3, R4, R5, R6, R7, R10, R11, R12 and R13, respectively, are unsubstituted or substituted by one or more radicals selected from the group consisting of halogen, nitro, hydroxy, cyano, NR10Rn, (C1-C4)-alkyl, (C1-C4)haloalkyl, (Ci-C4)-alkoxy, (Ci-C4)-haloalkoxy, (Ci-C4)-alkylthio, (Ci-C4)-alkylsulfoxy, (C1-C4)alkylsulfone, (Ci-C4)-haloalkylthio, (Ci-C4)-haloalkylsulfoxy, (Ci-C4)-haloalkylsulfone, (CiC4)-alkoxycarbonyl, (Ci-C4)-haloalkoxycarbonyl, (Ci-C4)-alkylcarboxy, (C3-C6)-cycloalkyl, (C3C6)-cycloalkyl-(Ci-C6)-alkyl, (Ci-C4)-alkoxycarbonyl-(Ci-C4)-alkyl, hydroxycarbonyl, hydroxycarbonyl-(Ci-C4)-alkyl, R10RnN-carbonyl, and where the structural elements cycloalkyl and heterocyclyl have n oxo groups, where n = 0, 1 or 2.
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  2. 2. The compound of the general formula (1) as claimed in claim 1 and/or the salt thereof, characterized in that
    Q represents the moieties Q-1 to Q-29
    s' 4/ \ 7 4/ \ 7 R4 R4 R R R R R R7 Q-1 Q-2 Q-3 Q-4 Q-5 N yr 4)=N °\V 4/ \ 7 R7 ~yr R4 V R4 R R R r4/ R7 Q-6 Q-7 Q-8 Q-9 Q-10 4/ N 4/ \ 7 p5 RNx 4/ ' 7 R7 ~yr 4/ '5 R4 AX' R4 R R R R R R r5/ r7 Q-11 Q-12 Q-13 Q-14 „4 Q-15 aLa4 A* V 'AfeN 4 «ζ V R«—/°\—— V R N—N V O' V -c Q-16 Q-17 Q-18 Q-19 Q-20
    Q-21 Q-22 Q-23 Q-25
    Q-26 Q-27 Q-28 Q-29
    A1, A2, A3, A4 are identical or different and independently of one another represent N (nitrogen) or the moiety C-R8, but there are never more than two adjacent nitrogen atoms, and where R8 in the moiety C-R8 in each case has identical or different meanings 10 according to the definition below,
    X and Y independently of one another represent C-H or the moiety C-R1, where
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    X represents C-H if Y represents the moiety C-R1 and
    X represents the moiety C-R1 if Y represents C-H,
    R1 represents halogen, (Ci-C7)-alkyl, (Ci-C7)-haloalkyl, (C1-C7)-hydroxyalkyl, (C1-C7)alkoxyalkyl, (Ci-C7)-alkoxy, (Ci-C7)-haloalkoxy, (Ci-C7)-alkylthio, (C1-C7)haloalkylthio, aryl, heteroaryl, aryloxy, heteroaryloxy, heterocyclyl, (C3-Cio)-cycloalkyl, (C3-Cio)-cycloalkyl-(Ci-C7)-alkyl, (C3-C7)-halocycloalkyl, (C3-C7)-halocycloalkyl-(CiC7)-alkyl, (Ci-C7)-alkylcarbonyl, (C2-C7)-alkenyl, (C2-C7)-alkynyl, tris-[(Ci-C7)alkyl]silyl-(C2-C7)-alkynyl, NR10Rn,
    R3 represents hydroxy, hydrothio, halogen, NR10RH, (Ci-C7)-alkoxy, (C3-Cio)-cycloalkyl(Ci-C7)-alkoxy, aryl-(Ci-C7)-alkoxy, (Ci-C7)-alkoxy-(Ci-C7)-alkoxy, arylcarbonyloxy, (Ci-C7)-alkylcarbonyloxy, aryl-(Ci-C7)-alkylcarbonyloxy, heteroarylcarbonyloxy, (C3Cio)-cycloalkylcarbonyloxy, heterocyclylcarbonyloxy, (Ci-C7)-haloalkylcarbonyloxy, (C2-C7)-alkenylcarbonyloxy, OC(O)OR12, OC(O)SR12, OC(S)OR12, OC(S)SR12, OSO2R13, OSO2OR12, OCHO,
    R4 and R7 independently of one another represent hydrogen, hydrothio, hydroxy, halogen, (CiC7)-alkyl, (Ci-C7)-haloalkyl, (C3-Cio)-cycloalkyl, (C3-Cio)-cycloalkyl-(Ci-C7)-alkyl, aryl, heteroaryl, heterocyclyl, aryl-(Ci-C7)-alkyl, heteroaryl-(Ci-C7)-alkyl, heterocyclyl(Ci-C7)-alkyl, (C2-C7)-alkenyl, (C2-C7)-alkynyl, (C2-C7)-haloalkenyl, (C2-C7)haloalkynyl, (C3-Cio)-halocycloalkyl, (C4-Cio)-cycloalkenyl, (C4-Cio)-halocycloalkenyl, aryl-(C2-C7)-alkenyl, heteroaryl-(C2-C7)-alkenyl, heterocyclyl-(C2-C7)-alkenyl, aryl-(C2C7)-alkynyl, heteroaryl-(C2-C7)-alkynyl, heterocyclyl-(C2-C7)-alkynyl, (C3-C10)cycloalkyl-(C2-C7)-alkynyl, arylcarbonyl-(Ci-C7)-alkyl, (Ci-C7)-alkylcarbonyl-(Ci-C7)alkyl, heteroarylcarbonyl-(Ci-C7)-alkyl, (C3-Cio)-cycloalkylcarbonyl-(Ci-C7)-alkyl, aryl(Ci-C7)-alkoxycarbonyl-(Ci-C7)-alkyl, (Ci-C7)-alkoxycarbonyl-(Ci-C7)-alkyl, (C1-C7)alkoxy-(Ci-C7)-alkyl, arylcarbonyloxy-(Ci-C7)-alkyl, heteroarylcarbonyloxy-(Ci-C7)alkyl, heterocyclylcarbonyloxy-(Ci-C7)-alkyl, (Ci-C7)-alkylcarbonyloxy-(Ci-C7)-alkyl, (C3-C7)-cycloalkylcarbonyloxy-(Ci-C7)-alkyl, (Ci-C7)-haloalkoxy-(Ci-C7)-alkyl, aryl(Ci-C7)-alkoxy-(Ci-C7)-alkyl, heteroaryl-(Ci-C7)-alkoxy-(Ci-C7)-alkyl, CHO, C(O)R12, C(O)OR12, C(O)NR10Rn, OR12, SR13, SOR13, SO2R13, NR10Rn, R10R11N-(Ci-C7)-alkyl, cyano-(Ci-C7)-alkyl, hydroxycarbonyl-(Ci-C7)-alkyl, hydroxycarbonyl, (C1-C7)haloalkoxy-(Ci-C7)-alkylthio, (Ci-C7)-alkylthio-(Ci-C7)-alkylene, (Ci-C7)-haloalkylthio(Ci-C7)-alkylthio, (Ci-C7)-alkylthio-(Ci-C7)-alkylthio, aminocarbonyl, aminocarbonyl(Ci-C7)-alkyl, (Ci-C7)-alkylaminocarbonyl-(Ci-C7)-alkyl, (C3-C7)cycloalkylaminocarbonyl-(Ci-C7)-alkyl, (C2-C7)-alkenyloxycarbonyl-(Ci-C7)-alkyl, (C3
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    C7)-cycloalkyl- (Ci-C7)-alkoxycarbonyl-(Ci-C7)-alkyl, cyano, hydroxy-(Ci-C7)-alkyl, (C2-C7)-alkenyloxy-(Ci-C7)-alkyl, or where R4 and R7 together with the carbon atom to which they are respectively attached form a partially saturated ring having a total of 3 to 7 members which is optionally interrupted by one to three heteroatoms from the group consisting of N, O and S and optionally substituted further, if Q represents Q-3, Q-4, Q-8, Q-9, Q-12 or Q19,
    R5 represents hydrogen, formyl, (Ci-C7)-alkyl, (Ci-C7)-haloalkyl, hydroxy-(Ci-C7)- alkyl, hydroxycarbonyl-(Ci-C7)-alkyl, (Ci-C7)-alkoxy-(Ci-C7)-alkyl, (C3-Cio)-cycloalkyl, (C3Cio)-halocycloalkyl, aryl, heteroaryl, (C3-Cio)-cycloalkyl-(Ci-C7)-alkyl, heterocyclyl, (C2-C7)-alkenyl, (C2-C7)-alkynyl, NR10RH, aryl-(Ci-C7)-alkyl, heteroaryl-(Ci-C7)-alkyl, heterocyclyl-(Ci-C7)-alkyl, (Ci-C7)-cyanoalkyl, C(O)R12, C(O)OR12, C(O)NR10R11, SO2R13, (Ci-C7)-alkoxycarbonyl-(Ci-C7)-alkyl, (C2-C7)-alkenyloxycarbonyl-(Ci-C7)alkyl, aryl-(Ci-C7)-alkoxycarbonyl-(Ci-C7)-alkyl, heteroaryl-(Ci-C7)-alkoxycarbonyl(Ci-C7)-alkyl, aryloxycarbonyl-(Ci-C7)-alkyl, arylcarbonyl-(Ci-C7)-alkyl, (C1-C7)alkylcarbonyl-(Ci-C7)-alkyl, heteroarylcarbonyl-(Ci-C7)-alkyl, heterocyclylcarbonyl(Ci-C7)-alkyl, or where R4 and R5 together with the nitrogen atom or carbon atom to which they are respectively attached form a partially saturated ring having a total of 3 to 7 members which is optionally interrupted by one to three heteroatoms from the group consisting of N, O and S and optionally substituted further, if Q represents Q-13, Q-14 or Q-15,
    R6 represents hydrogen or (Ci-C7)-alkyl,
    R8 represents hydrogen, halogen, cyano, nitro, hydrothio, hydroxy, NR10RH, OR12, SR13, SOR13, SO2R13, thiocyanate, isothiocyanate, formyl, (Ci-C7)-alkyl, (C2-C7)-alkenyl, (C2C7)-alkynyl, (Ci-Cio)-haloalkyl, (C2-C7)-haloalkenyl, (C2-C7)-haloalkynyl, (C3-C10)cycloalkyl, (C3-Cio)-halocycloalkyl, (C4-Cio)-cycloalkenyl, (C4-Cio)-halocycloalkenyl, pentafluorothio, (Ci-C7)-alkoxy-(Ci-C7)-haloalkyl, (Ci-C7)-haloalkoxy-(Ci-C7)haloalkyl, (Ci-C7)-haloalkoxy-(Ci-C7)-alkyl, aryl, aryl-(Ci-C7)-alkyl, heteroaryl, heteroaryl-(Ci-C7)-alkyl, (C3-C7)-cycloalkyl-(Ci-C7)-alkyl, (C4-Cio)-cycloalkenyl-(CiC7)-alkyl, heterocyclyl, heterocyclyl-(Ci-C7)-alkyl, (Ci-C7)-alkoxy-(Ci-C7)-alkyl, (CiC7)-alkylthio-(Ci-C7)-alkyl, (Ci-C7)-haloalkylthio-(Ci-C7)-alkyl, (Ci-C7)-alkylcarbonyl(Ci-C7)-alkyl, C(O)OR12, C(O)NR10Rn, C(O)R12, -C=NOR12,
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    -C=NOH, R10RnN-(Ci-C7)-alkyl, R12O(O)C-(Ci-C7)-alkyl, hydroxycarbonyl, hydroxycarbonyl-(Ci-C7)-alkyl, aryl-(Ci-C7)-alkynyl, heteroaryl-(Ci-C7)-alkynyl, heterocyclyl-(Ci-C7)-alkynyl, tris-[(Ci-C7)-alkyl]silyl-(C2-C7)-alkynyl, bis-[(Ci-C7)alkyl](aryl)silyl-(C2-C7)-alkynyl, bis-aryl[(Ci-C7)-alkyl]silyl-(C2-C7)-alkynyl, (C3-C7)cycloalkyl-(C2-C7)-alkynyl, aryl-(C2-C7)-alkenyl, heteroaryl-(C2-C7)-alkenyl, heterocyclyl-(C2-C7)-alkenyl, (C3-C7)-cycloalkyl-(C2-C7)-alkenyl, (Ci-C7)-alkoxy-(CiC7)-alkoxy-(Ci-C7)-alkyl, (Ci-C7)-alkylaminosulfonylamino, (C3-C7)cycloalkylaminosulfonylamino, diazo, aryldiazo, tris-[(Ci-C7)-alkyl]silyl, bis-[(Ci-C7)alkyl] (aryl)silyl, bis-aryl[(Ci -C7)-alky 1]silyl, or where A1 and A2, when each is a group C-R8, together with the atoms to which they are attached form a partially saturated or fully unsaturated 5- to 7-membered ring which is optionally interrupted by heteroatoms from the group consisting of N, O and S and optionally substituted further, or where A2 and A3, when each is a group C-R8, together with the atoms to which they are attached form a partially saturated or fully unsaturated 5- to 7-membered ring which is optionally interrupted by heteroatoms from the group consisting of N, O and S and optionally substituted further, or where A3 and A4, when each is a group C-R8, together with the atoms to which they are attached form a partially saturated or fully unsaturated 5- to 7-membered ring which is optionally interrupted by heteroatoms from the group consisting of N, O and S and optionally substituted further,
    R10 and R11 are identical or different and independently of one another represent hydrogen, (CiC7)-alkyl, (C2-C7)-alkenyl, (C2-C7)-alkynyl, (Ci-C7)-cyanoalkyl, (Ci-Cio)-haloalkyl, (C2C7)-haloalkenyl, (C2-C7)-haloalkynyl, (C3-Cio)-cycloalkyl, (C3-Cio)-halocycloalkyl, (C4Cio)-cycloalkenyl, (C4-Cio)-halocycloalkenyl, (Ci-C7)-alkoxy-(Ci-C7)-alkyl, (Ci-C7)haloalkoxy-(Ci-C7)-alkyl, (Ci-C7)-alkyltitio-(Ci-C7)-alkyl, (Ci-C7)-haloalkyltitio-(CiC7)-alkyl, (Ci-C7)-alkoxy-(Ci-C7)-haloalkyl, aryl, aryl-(Ci-C7)-alkyl, heteroaryl, heteroaryl-(Ci-C7)-alkyl, (C3-Cio)-cycloalkyl-(Ci-C7)-alkyl, (C4-Cio)-cycloalkenyl-(CiC7)-alkyl, COR12, SO2R13, (Ci-C7)-alkyl-HNO2S-, (C3-Cio)-cycloalkyl-HN02S-, heterocyclyl, (Ci-C7)-alkoxycarbonyl-(Ci-C7)-alkyl, (Ci-C7)-alkoxycarbonyl, aryl-(CiC7)-alkoxycarbonyl-(Ci-C7)-alkyl, aryl-(Ci-C7)-alkoxycarbonyl, heteroaryl-(Ci-C7)alkoxycarbonyl, (C2-C7)-alkenyloxycarbonyl, (C2-C7)-alkynyloxycarbonyl, heterocyclyl(Ci-C7)-alkyl,
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    R12 represents (Ci-C7)-alkyl, (C2-C?)-alkenyl, (C2-C?)-alkynyl, (Ci-C7)-cyanoalkyl, (Ci-Cio)haloalkyl, (C2-C7)-haloalkenyl, (C2-C7)-haloalkynyl, (C3-Cio)-cycloalkyl, (C3-C10)halocycloalkyl, (C4-Cio)-cycloalkenyl, (C4-Cio)-halocycloalkenyl, (Ci-C7)-alkoxy-(CiC7)-alkyl, (Ci-C7)-alkoxy-(Ci-C7)-haloalkyl, aryl, aryl-(Ci-C7)-alkyl, heteroaryl, heteroaryl-(Ci-C7)-alkyl, (C3-Cio)-cycloalkyl-(Ci-C7)-alkyl, (C4-Cio)-cycloalkenyl-(CiC7)-alkyl, (Ci-C7)-alkoxycarbonyl-(Ci-C7)-alkyl, (C2-C7)-alkenyloxycarbonyl-(Ci-C7)alkyl, aryl-(Ci-C7)-alkoxycarbonyl-(Ci-C7)-alkyl, hydroxycarbonyl-(Ci-C7)-alkyl, heterocyclyl, heterocyclyl-(Ci-C7)-alkyl,
    R13 represents (Ci-C7)-alkyl, (C2-C7)-alkenyl, (C2-C7)-alkynyl, (Ci-C7)-cyanoalkyl, (C1-C10)haloalkyl, (C2-C7)-haloalkenyl, (C2-C7)-haloalkynyl, (C3-Cio)-cycloalkyl, (C3-C10)halocycloalkyl, (C4-Cio)-cycloalkenyl, (C4-Cio)-halocycloalkenyl, (Ci-C7)-alkoxy-(CiC7)-alkyl, (Ci-C7)-alkoxy-(Ci-C7)-haloalkyl, aryl, aryl-(Ci-C7)-alkyl, heteroaryl, heteroaryl-(Ci-C7)-alkyl, heterocyclyl-(Ci-C7)-alkyl, (C3-Cio)-cycloalkyl-(Ci-C7)-alkyl, (C4-Cio)-cycloalkenyl-(Ci-C7)-alkyl, NR'V, and
    W represents oxygen or sulfur.
  3. 3. The compound of the general formula (I) as claimed in claim 1 and/or the salt thereof, characterized in that
    Q represents the groups Q-l to Q-29
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    A1, A2, A3, A4 are identical or different and independently of one another represent N (nitrogen) or the moiety C-R8, but there are never more than two adjacent nitrogen
    5 atoms, and where R8 in the moiety C-R8 in each case has identical or different meanings according to the definition below,
    X and Y independently of one another represent C-H or the moiety C-R1, where
    X represents C-H if Y represents the moiety C-R1 and
    X represents the moiety C-R1 if Y represents C-H,
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    R1 represents halogen, (Ci-Cej-alkyl, (Ci-Cej-haloalkyl, (Ci-Ce)-hydroxyalkyl, (Ci-Ce)alkoxyalkyl, (Ci-Cej-alkoxy, (Ci-Cej-haloalkoxy, (Ci-Cej-alkylthio, (Ci-Ce)haloalkylthio, aryl, heteroaryl, aryloxy, heteroaryloxy, heterocyclyl, (C3-Cio)-cycloalkyl, (C3-Cio)-cycloalkyl-(Ci-C6)-alkyl, (C3-C6)-halocycloalkyl, (C3-C6)-halocycloalkyl-(CiCej-alkyl, (Ci-Cej-alkylcarbonyl, (Cz-Cej-alkenyl, (Cz-Cej-alkynyl, tris-f/Ci-Ce)alkyl]silyl-(C2-C6)-alkynyl, NR10Rn,
    R3 represents hydroxy, hydrothio, halogen, NR10RH, (Ci-Cej-alkoxy, (C3-Cio)-cycloalkyl(Ci-Cej-alkoxy, aryl-(Ci-C6)-alkoxy, (Ci-C6)-alkoxy-(Ci-C6)-alkoxy, arylcarbonyloxy, (Ci-Cej-alkylcarbonyloxy, aryl-(Ci-C6)-alkylcarbonyloxy, heteroarylcarbonyloxy, (C3Cio)-cycloalkylcarbonyloxy, heterocyclylcarbonyloxy, (Ci-Cej-haloalkylcarbonyloxy, (C2-C6)-alkenylcarbonyloxy, OC(O)OR12, OC(O)SR12, OC(S)OR12, OC(S)SR12, OSO2R13, OSO2OR12, OCHO,
    R4 and R7 independently of one another represent hydrogen, hydrothio, hydroxy, halogen, (CiCej-alkyl, (Ci-Cej-haloalkyl, (C3-Cio)-cycloalkyl, (C3-Cio)-cycloalkyl-(Ci-C6)-alkyl, aryl, heteroaryl, heterocyclyl, aryl-(Ci-C6)-alkyl, heteroaryl-(Ci-C6)-alkyl, heterocyclyl(Ci-Cej-alkyl, (C2-C6)-alkenyl, (C2-C6)-alkynyl, (C2-C6)-haloalkenyl, (C2-C6)haloalkynyl, (C3-Cio)-halocycloalkyl, (C4-Cio)-cycloalkenyl, (C4-Cio)-halocycloalkenyl, aryl-(C2-C6)-alkenyl, heteroaryl-(C2-C6)-alkenyl, heterocyclyl-(C2-C6)-alkenyl, aryl-(C2Cej-alkynyl, heteroaryl-(C2-C6)-alkynyl, heterocyclyl-(C2-C6)-alkynyl, (C3-C10)cycloalkyl-(C2-C6)-alkynyl, arylcarbonyl-(Ci-C6)-alkyl, (Ci-Cej-alkylcarbonyh/Ci-Ce)alkyl, heteroarylcarbonyl-(Ci-C6)-alkyl, (C3-Cio)-cycloalkylcarbonyl-(Ci-C6)-alkyl, aryl(Ci-Cej-alkoxycarbonyh/Ci-Cej-alkyl, (Ci-Cej-alkoxycarbonyh/Ci-Cej-alkyl, (Ci-Ce)alkoxy-(Ci-C6)-alkyl, arylcarbonyloxy-(Ci-C6)-alkyl, heteroarylcarbonyloxy-(Ci-C6)alkyl, heterocyclylcarbonyloxy-(Ci-C6)-alkyl, (Ci-C6)-alkylcarbonyloxy-(Ci-C6)-alkyl, (C3-C6)-cycloalkylcarbonyloxy-(Ci-C6)-alkyl, (Ci-C6)-haloalkoxy-(Ci-C6)-alkyl, aryl(Ci-C6)-alkoxy-(Ci-C6)-alkyl, heteroaryl-(Ci-C6)-alkoxy-(Ci-C6)-alkyl, CHO, C(O)R12, C(O)OR12, C(O)NR10Rn, OR12, SR13, SOR13, SO2R13, NR10Rn, R10R11N-(Ci-C6)-alkyl, cyano-(Ci-C6)-alkyl, hydroxycarbonyl-(Ci-C6)-alkyl, hydroxycarbonyl, (Ci-Ce)haloalkoxy-(Ci-C6)-alkylthio, (Ci-C6)-alkylthio-(Ci-C6)-alkylene, (Ci-Cej-haloalkylthio(Ci-Cej-alkylthio, (Ci-C6)-alkylthio-(Ci-C6)-alkylthio, aminocarbonyl, aminocarbonyl(Ci-Cej-alkyl, (Ci-C6)-alkylaminocarbonyl-(Ci-C6)-alkyl, (C3-C6)cycloalkylaminocarbonyl-(Ci-C6)-alkyl, (C2-C6)-alkenyloxycarbonyl-(Ci-C6)-alkyl, (C3C6)-cycloalkyl-(Ci-C6)-alkoxycarbonyl-(Ci-C6)-alkyl, cyano, hydroxy-(Ci-C6)-alkyl, (C2-C6)-alkenyloxy-(Ci-C6)-alkyl,
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    208 or where R4 and R7 together with the carbon atom to which they are respectively attached form a partially saturated ring having a total of 3 to 7 members which is optionally interrupted by one to three heteroatoms from the group consisting of N, O and S and optionally substituted further, if Q represents Q-3, Q-4, Q-8, Q-9, Q-12 or Q19,
    R5 represents hydrogen, formyl, (Ci-Cej-alkyl, (Ci-Cej-haloalkyl, hydroxy-(Ci-C6)- alkyl, hydroxycarbonyl-(Ci-C6)-alkyl, (Ci-C6)-alkoxy-(Ci-C6)-alkyl, (C3-Cio)-cycloalkyl, (C3Cio)-halocycloalkyl, aryl, heteroaryl, (C3-Cio)-cycloalkyl-(Ci-C6)-alkyl, heterocyclyl, (C2-C6)-alkenyl, (C2-C6)-alkynyl, NR10RH, aryl-(Ci-C6)-alkyl, heteroaryl-(Ci-C6)-alkyl, heterocyclyl-(Ci-C6)-alkyl, (Ci-Ce)-cyanoalkyl, C(O)R12, C(O)OR12, C(O)NR10R11, SO2R13, (Ci-Cej-alkoxycarbonyh/Ci-Cej-alkyl, (C2-C6)-alkenyloxycarbonyl-(Ci-C6)alkyl, aryl-(Ci-C6)-alkoxycarbonyl-(Ci-C6)-alkyl, heteroaryl-(Ci-C6)-alkoxycarbonyl(Ci-Cej-alkyl, aryloxycarbonyl-(Ci-C6)-alkyl, arylcarbonyl-(Ci-C6)-alkyl, (Ci-Ce)alkylcarbonyl-(Ci-C6)-alkyl, heteroarylcarbonyl-(Ci-C6)-alkyl, heterocyclylcarbonyl(Ci-C6)-alkyl, or where R4 and R5 together with the nitrogen atom or carbon atom to which they are respectively attached form a partially saturated ring having a total of 3 to 7 members which is optionally interrupted by one to three heteroatoms from the group consisting of N, O and S and optionally substituted further, if Q represents Q-13, Q-14 or Q-15,
    R6 represents hydrogen or (Ci-Cej-alkyl,
    R8 represents hydrogen, halogen, cyano, nitro, hydrothio, hydroxy, NR10RH, OR12, SR13, SOR13, SO2R13, thiocyanate, isothiocyanate, formyl, (Ci-Cej-alkyl, (C2-C6)-alkenyl, (C2Cej-alkynyl, (Ci-Cio)-haloalkyl, (C2-C6)-haloalkenyl, (C2-C6)-haloalkynyl, (C3-C10)cycloalkyl, (C3-Cio)-halocycloalkyl, (C4-Cio)-cycloalkenyl, (C4-Cio)-halocycloalkenyl, pentafluorothio, (Ci-C6)-alkoxy-(Ci-C6)-haloalkyl, (Ci-C6)-haloalkoxy-(Ci-C6)haloalkyl, (Ci-C6)-haloalkoxy-(Ci-C6)-alkyl, aryl, aryl-(Ci-C6)-alkyl, heteroaryl, heteroaryl-(Ci-C6)-alkyl, (C3-C6)-cycloalkyl-(Ci-C6)-alkyl, (C4-Cio)-cycloalkenyl-(CiCej-alkyl, heterocyclyl, heterocyclyl-(Ci-C6)-alkyl, (Ci-C6)-alkoxy-(Ci-C6)-alkyl, (CiC6)-alkylthio-(Ci-C6)-alkyl, (Ci-C6)-haloalkylthio-(Ci-C6)-alkyl, (Ci-Cej-alkylcarbonyl(Ci-Ce)-alkyl, C(O)OR12, C(O)NR10Rn, C(O)R12, -C=NOR12, -C=NOH, R10RnN-(CiCej-alkyl, R12O(O)C-(Ci-C6)-alkyl, hydroxycarbonyl, hydroxycarbonyl-(Ci-C6)-alkyl, aryl-(Ci-C6)-alkynyl, heteroaryl-(Ci-C6)-alkynyl, heterocyclyl-(Ci-C6)-alkynyl, tris-[(CiC6)-alkyl]silyl-(C2-C6)-alkynyl, bis-[(Ci-C6)-alkyl](aryl)silyl-(C2-C6)-alkynyl, bis
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    209 aryl[(Ci-C6)-alkyl]silyl-(C2-C6)-alkynyl, (C3-C6)-cycloalkyl-(C2-C6)-alkynyl, aryl-(C2Cej-alkenyl, heteroaryl-(C2-C6)-alkenyl, heterocyclyl-(C2-C6)-alkenyl, (C3-C6)cycloalkyl-(C2-C6)-alkenyl, (Ci-C6)-alkoxy-(Ci-C6)-alkoxy-(Ci-C6)-alkyl, (Ci-Ce)alkylaminosulfonylamino, (C3-C6)-cycloalkylaminosulfonylamino, diazo, aryldiazo, tris[(Ci-Cej-alkylJsilyl, bis-[(Ci-C6)-alkyl](aryl)silyl, bis-aryl[(Ci-C6)-alkyl]silyl, or where A1 and A2, when each is a group C-R8, together with the atoms to which they are attached form a partially saturated or fully unsaturated 5- to 7-membered ring which is optionally interrupted by heteroatoms from the group consisting of N, O and S and optionally substituted further, or where A2 and A3, when each is a group C-R8, together with the atoms to which they are attached form a partially saturated or fully unsaturated 5- to 7-membered ring which is optionally interrupted by heteroatoms from the group consisting of N, O and S and optionally substituted further, or where A3 and A4, when each is a group C-R8, together with the atoms to which they are attached form a partially saturated or fully unsaturated 5- to 7-membered ring which is optionally interrupted by heteroatoms from the group consisting of N, O and S and optionally substituted further,
    R10 and R11 are identical or different and independently of one another represent hydrogen, (CiCej-alkyl, (C2-C6)-alkenyl, (C2-C6)-alkynyl, (Ci-Cej-cyanoalkyl, (Ci-Cio)-haloalkyl, (C2Cej-haloalkenyl, (C2-C6)-haloalkynyl, (C3-Cio)-cycloalkyl, (C3-Cio)-halocycloalkyl, (C4Cio)-cycloalkenyl, (C4-Cio)-halocycloalkenyl, (Ci-C6)-alkoxy-(Ci-C6)-alkyl, (Ci-Ce)haloalkoxy-(Ci-C6)-alkyl, (Ci-C6)-alkyltitio-(Ci-C6)-alkyl, (Ci-C6)-haloalkyltitio-(CiCej-alkyl, (Ci-C6)-alkoxy-(Ci-C6)-haloalkyl, aryl, aryl-(Ci-C6)-alkyl, heteroaryl, heteroaryl-(Ci-C6)-alkyl, (C3-Cio)-cycloalkyl-(Ci-C6)-alkyl, (C4-Cio)-cycloalkenyl-(CiC6)-alkyl, COR12, SO2R13, (Ci-C6)-alkyl-HNO2S-, (C3-Cio)-cycloalkyl-HN02S-, heterocyclyl, (Ci-Cej-alkoxycarbonyh/Ci-Cej-alkyl, (Ci-Cej-alkoxycarbonyl, aryl-(CiCej-alkoxycarbonyh/Ci-Cej-alkyl, aryl-(Ci-C6)-alkoxycarbonyl, heteroaryh/Ci-Ce)alkoxycarbonyl, (C2-C6)-alkenyloxycarbonyl, (C2-C6)-alkynyloxycarbonyl, heterocyclyl(Ci-C6)-alkyl,
    R12 represents (Ci-Cej-alkyl, (C2-C6)-alkenyl, (C2-C6)-alkynyl, (Ci-Cej-cyanoalkyl, (C1-C10)haloalkyl, (C2-C6)-haloalkenyl, (C2-C6)-haloalkynyl, (C3-Cio)-cycloalkyl, (C3-C10)halocycloalkyl, (C4-Cio)-cycloalkenyl, (C4-Cio)-halocycloalkenyl, (Ci-C6)-alkoxy-(CiWO 2018/114596
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    Cej-alkyl, (Ci-C6)-alkoxy-(Ci-C6)-haloalkyl, aryl, aryl-(Ci-C6)-alkyl, heteroaryl, heteroaryl-(Ci-C6)-alkyl, (C3-Cio)-cycloalkyl-(Ci-C6)-alkyl, (C4-Cio)-cycloalkenyl-(CiCej-alkyl, (Ci-Cej-alkoxycarbonyh/Ci-Cej-alkyl, (Cz-Cej-alkenyloxycarbonyh/Ci-Ce)alkyl, aryl-(Ci-C6)-alkoxycarbonyl-(Ci-C6)-alkyl, hydroxycarbonyl-(Ci-C6)-alkyl, heterocyclyl, heterocyclyl-(Ci-C6)-alkyl,
    R13 represents (Ci-Cej-alkyl, (Cz-Cej-alkenyl, (Cz-Cej-alkynyl, (Ci-Cej-cyanoalkyl, (Ci-Cio)haloalkyl, (Cz-Cej-haloalkenyl, (Cz-Cej-haloalkynyl, (C3-Cio)-cycloalkyl, (C3-C10)halocycloalkyl, (C4-Cio)-cycloalkenyl, (C4-Cio)-halocycloalkenyl, (Ci-C6)-alkoxy-(CiCej-alkyl, (Ci-C6)-alkoxy-(Ci-C6)-haloalkyl, aryl, aryl-(Ci-C6)-alkyl, heteroaryl, heteroaryl-(Ci-C6)-alkyl, heterocyclyl-(Ci-C6)-alkyl, (C3-Cio)-cycloalkyl-(Ci-C6)-alkyl, (C4-Cio)-cycloalkenyl-(Ci-C6)-alkyl, NR'V and
    W represents oxygen or sulfur.
  4. 4. The compound of the general formula (I) as claimed in claim 1 and/or the salt thereof, characterized in that
    Q represents the groups Q-l to Q-29
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    A1, A2, A3, A4 are identical or different and independently of one another represent N (nitrogen) or the moiety C-R8, but there are never more than two adjacent nitrogen
  5. 5 atoms, and where R8 in the moiety C-R8 in each case has identical or different meanings according to the definition above,
    X and Y independently of one another represent C-H or the moiety C-R1, where
    X represents C-H if Y represents the moiety C-R1 and
    X represents the moiety C-R1 if Y represents C-H,
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    R1 represents fluorine, chlorine, bromine, iodine, methyl, ethyl, n-propyl, 1 -methylethyl, nbutyl, 1 -methylpropyl, 2-methylpropyl, 1,1 -dimethylethyl, n-pentyl, 1 -methylbutyl, 2methylbutyl, 3-methylbutyl, 1,1-dimethylpropyl, 1,2-dimethylpropyl, 2,2dimethylpropyl, 1-ethylpropyl, n-hexyl, 1-methylpentyl, 2-methylpentyl, 3methylpentyl, 4-methylpentyl, 1,1-dimethylbutyl, 1,2-dimethylbutyl, 1,3-dimethylbutyl,
    2.2- dimethylbutyl, 2,3-dimethylbutyl, 3,3-dimethylbutyl, 1-ethylbutyl, 2-ethylbutyl,
    1.1.2- trimethylpropyl, 1,2,2-trimethylpropyl, 1-ethyl-1-methylpropyl, 1-ethyl-2methylpropyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, spiro[2.2]pent-l-yl, spiro[2.3]hex-l-yl, spiro[2.3]hex-4-yl, 3-spiro[2.3]hex-5-yl, spiro[3.3]hept-l-yl, spiro[3.3]hept-2-yl, bicyclo[ 1.1,0]butan-l -yl, bicyclo[ 1.1,0]butan-2-yl, bicyclo[2.1,0]pentan-1 -yl, bicyclo[ 1.1.1 ]pentan-1 -yl, bicyclo[2.1,0]pentan-2-yl, bicyclo[2.1,0]pentan-5-yl, bicyclo[2.1.1 ]hexyl, bicyclo[2.2.1 ]hept-2-yl, bicyclo[2.2.2]octan-2-yl, bicyclo[3.2.1]octan-2-yl, bicyclo[3.2.2]nonan-2-yl, adamantan-l-yl, adamantan-2-yl, 1-methylcyclopropyl, 2-methylcyclopropyl, 2,2dimethylcyclopropyl, 2,3-dimethylcyclopropyl, l,l'-bi(cyclopropyl)-l-yl, 1,1'bi(cyclopropyl)-2-yl, 2'-methyl-l,l'-bi(cyclopropyl)-2-yl, 1-cyanocyclopropyl, 2cyanocyclopropyl, 1-methylcyclobutyl, 2-methylcyclobutyl, 3-methylcyclobutyl, 3,3dimethylcyclobut-1-yl, 1-cyanocyclobutyl, 2-cyanocyclobutyl, 3-cyanocyclobutyl, 3,3difluorocyclobut-l-yl, 3-fluorocyclobut-l-yl, 2,2-difluorocycloprop-1-yl, 1fluorocycloprop-l-yl, 2-fluorocycloprop-1-yl, 1-allylcyclopropyl, 1-vinylcyclobutyl, 1vinylcyclopropyl, 1-ethylcyclopropyl, 1-methylcyclohexyl, 2-methylcyclohexyl, 3methylcyclohexyl, 1-methoxycyclohexyl, 2-methoxycyclohexyl, 3-methoxycyclohexyl, trifluoromethyl, pentafluoroethyl, 1,1,2,2-tetrafluoroethyl, heptafluoropropyl, nonafluorobutyl, chlorodifluoromethyl, bromodifluoromethyl, dichlorofluoromethyl, iododifluoromethyl, bromo fluoromethyl, 1 -fluoroethyl, 2-fluoroethyl, fluoromethyl, difluoromethyl, 2,2-difluoroethyl, 2,2,2-trifluoroethyl, difluoro-tert-butyl, chloromethyl, bromomethyl, hydroxymethyl, hydroxyethyl, hydroxy-n-propyl, methoxy, ethoxy, npropyloxy, isopropyloxy, n-butyloxy, tert-butyloxy, methoxymethyl, ethoxymethyl, npropyloxymethyl, isopropyloxymethyl, methoxyethyl, ethoxyethyl, n-propyloxyethyl, isopropyloxyethyl, trifluoromethoxy, difluoromethoxy, pentafluoroethoxy, 2,2,1,1tetrafluoroethoxy, 2,2,2-trifluoroethoxy, 2,2-difluoroethoxy, methylthio, ethylthio, npropylthio, isopropylthio, trifluoromethylthio, pentafluoroethylthio, phenyl, 2fluorophenyl, 3-fluorophenyl, 4-fluorophenyl, 2,4-difluorophenyl, 2,5-difluorophenyl, 2,6-difluorophenyl, 2,3-difluorophenyl, 3,4-difluorophenyl, 3,5-difluorophenyl, 2,4,5trifluorophenyl, 3,4,5-trifluorophenyl, 2-chlorophenyl, 3-chlorophenyl, 4-chlorophenyl,
    2,4-dichlorophenyl, 2,5-dichlorophenyl, 2,6-dichlorophenyl, 2,3-dichlorophenyl, 3,4dichlorophenyl, 3,5-dichlorophenyl, 2,4,5-trichlorophenyl, 3,4,5-trichlorophenyl, 2,4,6
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    213 trichlorophenyl, 2-bromophenyl, 3-bromophenyl, 4-bromophenyl, 2-iodophenyl, 3iodophenyl, 4-iodophenyl, 2-bromo-4-fluorophenyl, 2-bromo-4-chlorophenyl, 3-bromo4-fluorophenyl, 3-bromo-4-chlorophenyl, 3-bromo-5-fluorophenyl, 3-bromo-5chlorophenyl, 2-fluoro-4-bromophenyl, 2-chloro-4-bromophenyl, 3-fluoro-4bromophenyl, 3-chloro-4-bromophenyl, 2-chloro-4-fluorophenyl, 3-chloro-4fluorophenyl, 2-fluoro-3-chlorophenyl, 2-fluoro-4-chlorophenyl, 2-fluoro-5chlorophenyl, 3-fluoro-4-chlorophenyl, 3-fluoro-5-chlorophenyl, 2-fluoro-6chlorophenyl, 2-methylphenyl, 3-methylphenyl, 4-methylphenyl, 2,4-dimethylphenyl,
    2.5- dimethylphenyl, 2,6-dimethylphenyl, 2,3-dimethylphenyl, 3,4-dimethylphenyl, 3,5dimethylphenyl, 2,4,5-trimethylphenyl, 3,4,5-trimethylphenyl, 2,4,6-trimethylphenyl, 2methoxyphenyl, 3-methoxyphenyl, 4-methoxyphenyl, 2,4-dimethoxyphenyl, 2,5dimethoxyphenyl, 2,6-dimethoxyphenyl, 2,3-dimethoxyphenyl, 3,4-dimethoxyphenyl,
    3.5- dimethoxyphenyl, 2,4,5-trimethoxyphenyl, 3,4,5-trimethoxyphenyl, 2,4,6trimethoxyphenyl, 2-trifluoromethoxyphenyl, 3-trifluoromethoxyphenyl, 4trifluoromethoxyphenyl, 2-difluoromethoxyphenyl, 3-difluoromethoxyphenyl, 4difluoromethoxyphenyl, 2-trifluoromethylphenyl, 3-trifluoromethylphenyl, 4trifluoromethylphenyl, 2-difluoromethylphenyl, 3-difluoromethylphenyl, 4difluoromethylphenyl, 3,5-bis(trifluoromethyl)-phenyl, 3 -trifluoromethyl-5fluorophenyl, 3-trifluoromethy 1-5-chlorophenyl, 3-methyl-5-fluorophenyl, 3-methyl-5chlorophenyl, 3-methoxy-5-fluorophenyl, 3-methoxy-5-chlorophenyl, 3trifluoromethoxy-5-chlorophenyl, 2-ethoxyphenyl, 3-ethoxyphenyl, 4-ethoxyphenyl, 2methylthiophenyl, 3-methylthiophenyl, 4-methylthiophenyl, 2trifluoromethylthiophenyl, 3 -trifluoromethylthiophenyl, 4-trifluoromethyhhiophenyl, phenyloxy, p-Clphenyloxy, thiophen-2-yl, thiophen-3-yl, pyridin-2-yl, pyridin-3-yl, pyridin-4-yl, furan-2-yl, furan-3-yl, tetrahydrofuran-2-yl, cyclopropylmethyl, cyclobutylmethyl, cyclopentylmethyl, cyclohexylmethyl, methylcarbonyl, ethylcarbonyl, n-propylcarbonyl, isopropylcarbonyl, n-butylcarbonyl, tert-butylcarbonyl, ethenyl, 1-propenyl, 2-propenyl, 1-methyl-ethenyl, l-butenyl, 2-butenyl, 3-butenyl, 1methyl-1-propenyl, 2-methyl-l-propenyl, 1-methyl-2-propenyl, 2-methyl-2-propenyl, 1pentenyl, 2-pentenyl, 3-pentenyl, 4-pentenyl, 1-methyl-1-butenyl, 2-methyl-1-butenyl,
    3-methyl-l-butenyl, 1-methyl-2-butenyl, 2-methyl-2-butenyl, 3-methyl-2-butenyl, 1methyl-3-butenyl, 2-methyl-3-butenyl, 3-methyl-3-butenyl, 1,1-dimethyl-2-propenyl,
    1,2-dimethyl-l-propenyl, 1,2-dimethyl-2-propenyl, 1-ethyl-1-propenyl, l-ethyl-2propenyl, 1-hexenyl, 2-hexenyl, 3-hexenyl, 4-hexenyl, 5-hexenyl, 1-methyl-1-pentenyl, 2-methyl-l-pentenyl, 3-methyl-1-pentenyl, 4-methyl-1-pentenyl, 1-methyl-2-pentenyl, 2-methyl-2-pentenyl, 3-methyl-2-pentenyl, 4-methyl-2-pentenyl, 1-methyl-3-pentenyl, 2-methyl-3-pentenyl, 3-methyl-3-pentenyl, 4-methyl-3-pentenyl, 1-methyl-4-pentenyl,
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    2-methyl-4-pentenyl, 3-methyl-4-pentenyl, 4-methyl-4-pentenyl, 1,1-dimethyl-2butenyl, l,l-dimethyl-3-butenyl, 1,2-dimethyl-1-butenyl, 1,2-dimethyl-2-butenyl, 1,2dimethyl-3-butenyl, 1,3-dimethyl-l-butenyl, l,3-dimethyl-2-butenyl, l,3-dimethyl-3butenyl, 2,2-dimethyl-3-butenyl, 2,3-dimethyl-l-butenyl, 2,3-dimethyl-2-butenyl, 2,3dimethyl-3-butenyl, 3,3-dimethyl-l-butenyl, 3,3-dimethyl-2-butenyl, 1-ethyl-1-butenyl, 1-ethyl-2-butenyl, l-ethyl-3-butenyl, 2-ethyl-1-butenyl, 2-ethyl-2-butenyl, 2-ethyl-3butenyl, 1,1,2-trimethyl-2-propenyl, 1-ethyl-1-methyl-2-propenyl, l-ethyl-2-methyl-lpropenyl and l-ethyl-2-methyl-2-propenyl, prop-2-en-1-yloxy, but-3-en-l-yloxy, pent4-en-l-yloxy, ethynyl, 1-propynyl, 2-propynyl, l-butynyl, 2-butynyl, 3-butynyl, 1methyl-2-propynyl, 1-pentynyl, 2-pentynyl, 3-pentynyl, 4-pentynyl, 1-methyl-2-butynyl, l-methyl-3-butynyl, 2-methyl-3-butynyl, 3-methyl-l-butynyl, 1,1-dimethyl-2-propynyl,
    1- ethyl-2-propynyl, 1-hexynyl, 2-hexynyl, 3-hexynyl, 4-hexynyl, 5-hexynyl, l-methyl-
    2- pentynyl, l-methyl-3-pentynyl, 1-methyl-4-pentynyl, 2-methyl-3-pentynyl, 2-methyl4-pentynyl, 3-methyl-1-pentynyl, 3-methyl-4-pentynyl, 4-methyl-1-pentynyl, 4-methyl2-pentynyl, 1,1-dimethyl-2-butynyl, l,l-dimethyl-3-butynyl, l,2-dimethyl-3-butynyl,
    2,2-dimethyl-3-butynyl, 3,3-dimethyl-l-butynyl, 1-ethyl-2-butynyl, l-ethyl-3-butynyl, 2-ethyl-3-butynyl, 1-ethyl-1-methyl-2-propynyl, 2-(trimethylsilyl)ethyn-l-yl, 2(triethylsilyl)ethyn-l-yl, 2-(triisopropylsilyl)ethyn-l-yl, amino, dimethylamino, diethylamino, methylamino, ethylamino, cyclopropylamino, n-propylamino, isopropylamino,
    R3 represents hydroxy, hydrothio, fluorine, chlorine, bromine, iodine, methoxy, ethoxy, npropyloxy, 1 -methylethoxy, n-butyloxy, 1 -methylpropyloxy, 2-methylpropyloxy, 1,1dimethylethoxy, n-pentyloxy, 1-methylbutyloxy, 2-methylbutyloxy, 3-methylbutyloxy, 1,1 -dimethylpropyloxy, 1,2-dimethylpropyloxy, 2,2-dimethylpropyloxy, 1 ethylpropyloxy, n-hexyloxy, 1-methylpentyloxy, 2-methylpentyloxy, 3methylpentyloxy, 4-methylpentyloxy, 1,1-dimethylbutyloxy, 1,2-dimethylbutyloxy, 1,3dimethylbutyloxy, 2,2-dimethylbutyloxy, 2,3-dimethylbutyloxy, 3,3-dimethylbutyloxy, 1-ethylbutyloxy, 2-ethylbutyloxy, 1,1,2-trimethylpropyloxy, 1,2,2-trimethylpropyloxy, 1 -ethyl-1 -methylpropyloxy, 1 -ethyl-2-methylpropyloxy, cyclopropylmethoxy, cyclobutylmethoxy, cyclopentylmethoxy, cyclohexylmethoxy, benzyloxy, pchlorophenylmethoxy, m-chlorophenylmethoxy, o-chlorophenylmethoxy, pmethoxyphenylmethoxy, p-nitrophenylmethoxy, methoxymethoxy, methoxyethoxy, methoxy-n-propyloxy, methoxy-n-butyloxy, ethoxymethoxy, ethoxyethoxy, ethoxy-npropyloxy, ethoxy-n-butyloxy, n-propyloxymethoxy, isopropyloxymethoxy, methylcarbonyloxy, ethylcarbonyloxy, n-propylcarbonyloxy, 1 -methylethylcarbonyloxy, n-butylcarbonyloxy, 1 -methylpropylcarbonyloxy, 2-methylpropylcarbonyloxy, 1,1
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    215 dimethylethylcarbonyloxy, n-pentylcarbonyloxy, 1 -methylbutylcarbonyloxy, 2methylbutylcarbonyloxy, 3-methylbutylcarbonyloxy, 1,1 -dimethylpropylcarbonyloxy,
    1.2- dimethylpropylcarbonyloxy, 2,2-dimethylpropylcarbonyloxy, 1 ethylpropylcarbonyloxy, n-hexylcarbonyloxy, 1-methylpentylcarbonyloxy, 2methylpentylcarbonyloxy, 3-methylpentylcarbonyloxy, 4-methylpentylcarbonyloxy, 1,1dimethylbutylcarbonyloxy, 1,2-dimethylbutylcarbonyloxy, 1,3dimethylbutylcarbonyloxy, 2,2-dimethylbutylcarbonyloxy, 2,3dimethylbutylcarbonyloxy, 3,3-dimethylbutylcarbonyloxy, 1-ethylbutylcarbonyloxy, 2ethylbutylcarbonyloxy, 1,1,2-trimethylpropylcarbonyloxy, 1,2,2trimethylpropylcarbonyloxy, 1 -ethyl-1 -methylpropylcarbonyloxy, 1 -ethyl-2methylpropylcarbonyloxy, phenylcarbonyloxy, p-chlorophenylcarbonyloxy, mchlorophenylcarbonyloxy, o-chlorophenylcarbonyloxy, p-fluorophenylcarbonyloxy, mfluorophenylcarbonyloxy, o-fluorophenylcarbonyloxy, benzylcarbonyloxy, thiophen-2ylcarbonyloxy, furan-2-ylcarbonyloxy, cyclopropylcarbonyloxy, cyclobutylcarbonyloxy, cyclopentylcarbonyloxy, cyclohexylcarbonyloxy, trifluoromethylcarbonyloxy, difluoromethylcarbonyloxy, methoxycarbonyloxy, ethoxycarbonyloxy, npropyloxycarbonyloxy, isopropyloxycarbonyloxy, n-butyloxycarbonyloxy, 1,1dimethylethyloxycarbonyloxy, 2,2-dimethylpropyloxycarbonyloxy, pyridin-2ylcarbonyloxy, pyridin-3-ylcarbonyloxy, pyridin-4-ylcarbonyloxy, 4trifluoromethylpyridin-3 -ylcarbonyloxy, allylcarbonyloxy, methylsulfonyloxy, ethylsulfonyloxy, n-propylsulfonyloxy, 1 -methylethylsulfonyloxy, cyclopropylsulfonyloxy cyclobutylsulfonyloxy, cyclopentylsulfonyloxy, cyclohexylsulfonyloxy, phenylsulfonyloxy, p-chlorophenylsulfonyloxy, mchlorophenylsulfonyloxy, o-chlorophenylsulfonyloxy, p-fluorophenylsulfonyloxy, mfluorophenylsulfonyloxy, o-fluorophenylsulfonyloxy, p-methoxyphenylsulfonyloxy, mmethoxyphenylsulfonyloxy, o-methoxyphenylsulfonyloxy, p-methylphenylsulfonyloxy, m-methylphenylsulfonyloxy, o-methylphenylsulfonyloxy,
    R4 and R7 independently of one another represent hydrogen, fluorine, chlorine, bromine, iodine, hydroxy, hydrothio, methyl, ethyl, n-propyl, 1-methylethyl, n-butyl, 1-methylpropyl, 2methylpropyl, 1,1-dimethylethyl, n-pentyl, 1-methylbutyl, 2-methylbutyl, 3methylbutyl, 1,1 -dimethylpropyl, 1,2-dimethylpropyl, 2,2-dimethylpropyl, 1 ethylpropyl, n-hexyl, 1-methylpentyl, 2-methylpentyl, 3-methylpentyl, 4-methylpentyl, 1,1-dimethylbutyl, 1,2-dimethylbutyl, 1,3-dimethylbutyl, 2,2-dimethylbutyl, 2,3dimethylbutyl, 3,3-dimethylbutyl, 1-ethylbutyl, 2-ethylbutyl, 1,1,2-trimethylpropyl,
    1.2.2- trimethylpropyl, 1 -ethyl-1 -methylpropyl, 1 -ethyl-2-methylpropyl, trifluoromethyl, pentafluoroethyl, 1,1,2,2-tetrafluoroethyl, heptafluoro-n-propyl, heptafluoroisopropyl,
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    216 nonafluorobutyl, chlorodifluoromethyl, bromodifluoromethyl, dichlorofluoromethyl, iododifluoromethyl, bromo fluoromethyl, 1 -fluoroethyl, 2-fluoroethyl, fluoromethyl, difluoromethyl, 2,2-difluoroethyl, 2,2,2-trifluoroethyl, difluoro-tert-butyl, chloromethyl, bromomethyl, fluoromethyl, 3,3,3-trifluoro-n-propyl, 1-fluoroprop-1-yl, 1trifluoromethylprop-l-yl, 2-trifluoromethylprop-2-yl, 1-fluoroprop-1-yl, 2-fluoroprop-2yl, 2-chloroprop-2-yl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, 1methylcycloprop-l-yl, 2-methylcycloprop-l-yl, 2,2-dimethylcycloprop-1-yl, 2,3dimethylcyclopropyl, 1-cyanocycloprop-1-yl, 2-cyanocycloprop-l-yl, 1methylcyclobutyl, 2-methylcyclobutyl, 3-methylcyclobutyl, 3,3-dimethylcyclobutyl, 1cyanocyclobutyl, 2-cyanocyclobutyl, 3-cyanocyclobutyl, 1-allylcyclopropyl, 1vinylcyclobutyl, 1 -vinylcyclopropyl, 1 -ethylcyclopropyl, 1 -methylcyclohexyl, 2methylcyclohexyl, 3-methylcyclohexyl, 1-methoxycyclohexyl, 2-methoxycyclohexyl, 3methoxycyclohexyl, spiro[2.2]pent-l-yl, spiro[2.3]hex-l-yl, spiro[2.3]hex-4-yl, 3spiro[2.3]hex-5-yl, spiro[3.3]hept-l-yl, spiro[3.3]hept-2-yl, bicyclo[1.1.0]butan-l-yl, bicyclo [1.1,0]butan-2-yl, bicyclo [2.1,0]pentan-1 -yl, bicyclo [1.1.1 ]pentan-l -yl, bicyclo[2.1,0]pentan-2-yl, bicyclo[2.1,0]pentan-5-yl, bicyclo[2.1.1 ]hexyl, bicyclo[2.2.1]hept-2-yl, bicyclo[2.2.2]octan-2-yl, bicyclo[3.2.1]octan-2-yl, bicyclo[3.2.2]nonan-2-yl, adamantan-l-yl, adamantan-2-yl, cyclopropylmethyl, cyclobutylmethyl, cyclopentylmethyl, cyclohexylmethyl, phenyl, 2-fluorophenyl, 3fluorophenyl, 4-fluorophenyl, 2,4-difluorophenyl, 2,5-difluorophenyl, 2,6difluorophenyl, 2,3-difluorophenyl, 3,4-difluorophenyl, 3,5-difluorophenyl, 2,4,5trifluorophenyl, 3,4,5-trifluorophenyl, 2-chlorophenyl, 3-chlorophenyl, 4-chlorophenyl,
    2.4- dichlorophenyl, 2,5-dichlorophenyl, 2,6-dichlorophenyl, 2,3-dichlorophenyl, 3,4dichlorophenyl, 3,5-dichlorophenyl, 2,4,5-trichlorophenyl, 3,4,5-trichlorophenyl, 2,4,6trichlorophenyl, 2-bromophenyl, 3-bromophenyl, 4-bromophenyl, 2-iodophenyl, 3iodophenyl, 4-iodophenyl, 2-bromo-4-fluorophenyl, 2-bromo-4-chlorophenyl, 3-bromo4-fluorophenyl, 3-bromo-4-chlorophenyl, 3-bromo-5-fluorophenyl, 3-bromo-5chlorophenyl, 2-fluoro-4-bromophenyl, 2-chloro-4-bromophenyl, 3-fluoro-4bromophenyl, 3-chloro-4-bromophenyl, 2-chloro-4-fluorophenyl, 3-chloro-4fluorophenyl, 2-fluoro-3-chlorophenyl, 2-fluoro-4-chlorophenyl, 2-fluoro-5chlorophenyl, 3-fluoro-4-chlorophenyl, 3-fluoro-5-chlorophenyl, 2-fluoro-6chlorophenyl, 2-methylphenyl, 3-methylphenyl, 4-methylphenyl, 2,4-dimethylphenyl,
    2.5- dimethylphenyl, 2,6-dimethylphenyl, 2,3-dimethylphenyl, 3,4-dimethylphenyl, 3,5dimethylphenyl, 2,4,5-trimethylphenyl, 3,4,5-trimethylphenyl, 2,4,6-trimethylphenyl, 2methoxyphenyl, 3-methoxyphenyl, 4-methoxyphenyl, 2,4-dimethoxyphenyl, 2,5dimethoxyphenyl, 2,6-dimethoxyphenyl, 2,3-dimethoxyphenyl, 3,4-dimethoxyphenyl,
    3.5- dimethoxyphenyl, 2,4,5-trimethoxyphenyl, 3,4,5-trimethoxyphenyl, 2,4,6
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    217 trimethoxyphenyl, 2-trifluoromethoxyphenyl, 3-trifluoromethoxyphenyl, 4trifluoromethoxyphenyl, 2-difluoromethoxyphenyl, 3-difluoromethoxyphenyl, 4difluoromethoxyphenyl, 2-trifluoromethylphenyl, 3-trifluoromethylphenyl, 4trifluoromethylphenyl, 2-difluoromethylphenyl, 3-difluoromethylphenyl, 4difluoromethylphenyl, 3,5-bis(trifluoromethyl)-phenyl, 3 -trifluoromethyl-5fluorophenyl, 3-trifluoromethy 1-5-chlorophenyl, 3-methyl-5-fluorophenyl, 3-methyl-5chlorophenyl, 3-methoxy-5-fluorophenyl, 3-methoxy-5-chlorophenyl, 3trifluoromethoxy-5-chlorophenyl, 2-ethoxyphenyl, 3-ethoxyphenyl, 4-ethoxyphenyl, 2methylthiophenyl, 3-methylthiophenyl, 4-methylthiophenyl, 2trifluoromethylthiophenyl, 3-trifluoromethylthiophenyl, 4-trifluoromethyhhiophenyl, 2ethylphenyl, 3-ethylphenyl, 4-ethylphenyl, 2-methoxycarbonylphenyl, 3methoxycarbonylphenyl, 4-methoxycarbonylphenyl, 2-ethoxycarbonylphenyl, 3ethoxycarbonylphenyl, 4-ethoxycarbonylphenyl, pyridin-2-yl, pyridin-3-yl, pyridin-4-yl, pyrazin-2-yl, pyridazin-3-yl, pyridazin-4-yl, pyrimidin-2-yl, pyrimidin-5-yl, pyrimidin-
    4- yl, pyridazin-3-ylmethyl, pyridazin-4-ylmethyl, pyrimidin-2-ylmethyl, pyrimidin-5ylmethyl, pyrimidin-4-ylmethyl, pyrazin-2-ylmethyl, 3-chloro-pyrazin-2-yl, 3-bromopyrazin-2-yl, 3-methoxy-pyrazin-2-yl, 3-ethoxy-pyrazin-2-yl, 3-trifluoromethylpyrazin2-yl, 3-cyanopyrazin-2-yl, naphth-2-yl, naphth-1-yl, quinolin-4-yl, quinolin-6-yl, quinolin-8-yl, quinolin-2-yl, quinoxalin-2-yl, 2-naphthylmethyl, 1-naphthylmethyl, quinolin-4-ylmethyl, quinolin-6-ylmethyl, quinolin-8-ylmethyl, quinolin-2-ylmethyl, quinoxalin-2-ylmethyl, pyrazin-2-ylmethyl, 4-chloropyridin-2-yl, 3-chloropyridin-4-yl, 2-chloropyridin-3-yl, 2-chloropyridin-4-yl, 2-chloropyridin-5-yl, 2,6-dichloropyridin-4yl, 3-chloropyridin-5-yl, 3,5-dichloropyridin-2-yl, 3-chloro-5-trifluoromethylpyridin-2yl, (4-chloropyridin-2-yl)methyl, (3-chloropyridin-4-yl)methyl, (2-chloropyridin-3yl)methyl, (2-chloropyridin-4-yl)methyl, (2-chloropyridin-5-yl)methyl, (2,6dichloropyridin-4-yl)methyl, (3 -chloropyridin-5 -yl)methyl, (3,5-dichloropyridin-2yl)methyl, thiophen-2-yl, thiophen-3-yl, 5-methylthiophen-2-yl, 5-ethylthiophen-2-yl, 5chlorothiophen-2-yl, 5-bromothiophen-2-yl, 4-methylthiophen-2-yl, 3-methyhhiophen2-yl, 5-fluorothiophen-3-yl, 3,5-dimethylthiophen-2-yl, 3-ethylthiophen-2-yl, 4,5dimethylthiophen-2-yl, 3,4-dimethylthiophen-2-yl, 4-chlorothiophen-2-yl, furan-2-yl, 5methylfuran-2-yl, 5-ethylfuran-2-yl, 5-methoxycarbonylfuran-2-yl, 5-chlorofuran-2-yl,
    5- bromofuran-2-yl, thiophan-2-yl, thiophan-3-yl, sulfolan-2-yl, sulfolan-3-yl, tetrahydrothiopyran-4-yl, tetrahydropyran-4-yl, tetrahydrofuran-2-yl, tetrahydrofuran-3yl, l-(4-methylphenyl)ethyl, l-(3-methylphenyl)ethyl, l-(2-methylphenyl)ethyl, 1-(4chlorophenyl)ethyl, l-(3-chlorophenyl)ethyl, l-(2-chlorophenyl)ethyl, benzyl, (4fluorophenyl)methyl, (3-fluorophenyl)methyl, (2-fluorophenyl)methyl, (2,4difluorophenyl)methyl, (3,5-difluorophenyl)methyl, (2,5-difluorophenyl)methyl, (2,6
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    218 difluorophenyl)methyl, (2,4,5-trifluorophenyl)methyl, (2,4,6-trifluorophenyl)methyl, (4chlorophenyl)methyl, (3-chlorophenyl)methyl, (2-chlorophenyl)methyl, (2,4dichlorophenyl)methyl, (3,5-dichlorophenyl)methyl, (2,5-dichlorophenyl)methyl, (2,6dichlorophenyl)methyl, (2,4,5-trichlorophenyl)methyl, (2,4,6-trichlorophenyl)methyl, (4-bromophenyl)methyl, (3-bromophenyl)methyl, (2-bromophenyl)methyl, (4iodophenyl)methyl, (3-iodophenyl)methyl, (2-iodophenyl)methyl, (3-chloro-5trifluoromethyl-pyridin-2-yl)methyl, (2-bromo-4-fluorophenyl)methyl, (2-bromo-4chlorophenyl)methyl, (3-bromo-4-fluorophenyl)methyl, (3-bromo-4chlorophenyl)methyl, (3-bromo-5-fluorophenyl)methyl, (3-bromo-5chlorophenyl)methyl, (2-fluoro-4-bromophenyl)methyl, (2-chloro-4bromophenyl)methyl, (3-fluoro-4-bromophenyl)methyl, (3-chloro-4bromophenyl)methyl, (2-chloro-4-fluorophenyl)methyl, (3-chloro-4fluorophenyl)methyl, (2-fluoro-3-chlorop henyl)methyl, (2-fluoro-4chlorophenyl)methyl, (2-fluoro-5-chlorophenyl)methyl, (3-fluoro-4chlorophenyl)methyl, (3-fluoro-5-chlorophenyl)methyl, (2-fluoro-6chlorophenyl)methyl, 2-phenyleth-1-yl, 3-trifluoromethyl-4-chlorophenyl, 3-chloro-4trifluoromethylphenyl, 2-chloro-4-trifluoromethylphenyl, 3,5-difluoropyridin-2-yl, (3,6dichloropyridin-2-yl)methyl, (4-trifluoromethylphenyl)methyl, (3trifluoromethylphenyl)methyl, (2-trifluoromethylphenyl)methyl, (4trifluoromethoxyphenyl)methyl, (3 -trifluoromethoxyphenyl)methyl, (2trifluoromethoxyphenyl)methyl, (4-methoxyphenyl)methyl, (3 -methoxyphenyl)methyl, (2-methoxyphenyl)methyl, (4-methylphenyl)methyl, (3-methylphenyl)methyl, (2methylphenyl)methyl, (4-cyanophenyl)methyl, (3-cyanophenyl)methyl, (2cyanophenyl)methyl, (2,4-diethylphenyl)methyl, (3,5-diethylphenyl)methyl, (3,4dimethylphenyl)methyl, (3,5-dimethoxyphenyl)methyl, 1-phenyleth-1-yl, l-(ochlorophenyl)eth-1-yl, l,3-thiazol-2-yl, 4-methyl-l,3-thiazol-2-yl, l,3-thiazol-2-yl, ethenyl, 1-propenyl, 2-propenyl, 1-methylethenyl, l-butenyl, 2-butenyl, 3-butenyl, 1methyl-1-propenyl, 2-methyl-l-propenyl, 1-methyl-2-propenyl, 2-methyl-2-propenyl, 1pentenyl, 2-pentenyl, 3-pentenyl, 4-pentenyl, 1-methyl-1-butenyl, 2-methyl-l-butenyl,
    3-methyl-l-butenyl, 1-methyl-2-butenyl, 2-methyl-2-butenyl, 3-methyl-2-butenyl, 1methyl-3-butenyl, 2-methyl-3-butenyl, 3-methyl-3-butenyl, 1,1-dimethyl-2-propenyl,
    1,2-dimethyl-l-propenyl, 1,2-dimethyl-2-propenyl, 1-ethyl-1-propenyl, l-ethyl-2propenyl, 1-hexenyl, 2-hexenyl, 3-hexenyl, 4-hexenyl, 5-hexenyl, 1-methyl-1-pentenyl, 2-methyl-l-pentenyl, 3-methyl-1-pentenyl, 4-methyl-1-pentenyl, 1-methyl-2-pentenyl, 2-methyl-2-pentenyl, 3-methyl-2-pentenyl, 4-methyl-2-pentenyl, 1-methyl-3-pentenyl, 2-methyl-3-pentenyl, 3-methyl-3-pentenyl, 4-methyl-3-pentenyl, 1-methyl-4-pentenyl, 2-methyl-4-pentenyl, 3-methyl-4-pentenyl, 4-methyl-4-pentenyl, 1,1-dimethyl-2
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    219 butenyl, l,l-dimethyl-3-butenyl, 1,2-dimethyl-1-butenyl, 1,2-dimethyl-2-butenyl, 1,2dimethyl-3-butenyl, 1,3-dimethyl-l-butenyl, l,3-dimethyl-2-butenyl, l,3-dimethyl-3butenyl, 2,2-dimethyl-3-butenyl, 2,3-dimethyl-l-butenyl, 2,3-dimethyl-2-butenyl, 2,3dimethyl-3-butenyl, 3,3-dimethyl-l-butenyl, 3,3-dimethyl-2-butenyl, 1-ethyl-1-butenyl,
    1- ethyl-2-butenyl, l-ethyl-3-butenyl, 2-ethyl-l-butenyl, 2-ethyl-2-butenyl, 2-ethyl-3butenyl, 1,1,2-trimethyl-2-propenyl, 1-ethyl-1-methyl-2-propenyl, l-ethyl-2-methyl-lpropenyl and 1-ethyl-2-methyl-2-propenyl, ethynyl, 1-propynyl, 2-propynyl, l-butynyl,
    2- butynyl, 3-butynyl, 1-methyl-2-propynyl, l-pentynyl, 2-pentynyl, 3-pentynyl, 4pentynyl, 1-methyl-2-butynyl, l-methyl-3-butynyl, 2-methyl-3-butynyl, 3-methyl-1butynyl, 1,1-dimethyl-2-propynyl, l-ethyl-2-propynyl, 1-hexynyl, 2-hexynyl, 3-hexynyl,
    3,3-difluorocyclobut-l-yl, 3-fluorocyclobut-l-yl, 1 -fluorocyclobut-1 -yl, 2,2difluorocycloprop-1 -yl, 1-fluorocycloprop-1-yl, 2-fluorocycloprop-l-yl, 4fluorocyclohexyl, 4,4-difluorocyclohexyl, methoxycarbonylmethyl, ethoxycarbonylmethyl, n-propyloxycarbonylmethyl, isopropyloxycarbonylmethyl, nbutyloxycarbonylmethyl, tert-butyloxycarbonylmethyl, methoxymethyl, ethoxymethyl, n-propyloxymethyl, isopropyloxymethyl, n-butyloxymethyl, methoxyethyl, ethoxyethyl, n-propyloxyethyl, isopropyloxyethyl, methoxy-n-propyl, methoxy-n-butyl, trifluoromethoxymethyl, difluoromethoxymethyl, 2,2-difluoroethoxymethyl, 2,2,2trifluoroethoxymethyl, trifluoromethoxyethyl, difluoromethoxyethyl, 2,2difluoroethoxyethyl, 2,2,2-trifluoroethoxyethyl, methoxycarbonyl, ethoxycarbonyl, npropyloxycarbonyl, isopropyloxycarbonyl, n-butyloxycarbonyl, tert-butyloxycarbonyl, allyloxy carbonyl, benzyloxycarbonyl, methylcarbonyl, ethylcarbonyl, n-propylcarbonyl, isopropylcarbonyl, n-butylcarbonyl, tert-butylcarbonyl, phenylcarbonyl, pchlorophenylcarbonyl, m-chlorophenylcarbonyl, o-chlorophenylcarbonyl, pfluorophenylcarbonyl, m-fluorophenylcarbonyl, o-fluorophenylcarbonyl, pmethoxyphenylcarbonyl, m-methoxyphenylcarbonyl, o-methoxyphenylcarbonyl, ptrifluoromethylphenylcarbonyl, m-trifluoromethylphenylcarbonyl, otrifluoromethylphenylcarbonyl, methoxy, ethoxy, n-propyloxy, isopropyloxy, benzyloxy, p-chlorophenylmethoxy, phenyloxy, p-chlorophenyloxy, mchlorophenyloxy, o-chlorophenyloxy, p-fluorophenyloxy, m-fluorophenyloxy, ofluorophenyloxy, p-methoxyphenyloxy, m-methoxyphenyloxy, o-methoxyphenyloxy, ptrifluoromethylphenyloxy, m-trifluoromethylphenyloxy, o-trifluoromethylphenyloxy, methylaminocarbonyl, ethylaminocarbonyl, n-propylaminocarbonyl, isopropylaminocarbonyl, cyclopropylaminocarbonyl, cyclobutylaminocarbonyl, cyclopentylaminocarbonyl, cyclohexylaminocarbonyl, cyclopropylmethylaminocarbonyl, cyclobutylmethylaminocarbonyl, cyclopentylmethylaminocarbonyl, cyclohexylmethylaminocarbonyl,
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    220 dimethylaminocarbonyl, diethylaminocarbonyl, benzylmethylaminocarbonyl, methylamino, dimethylamino, ethylamino, diethylamino, n-propylamino, isopropylamino, cyclopropylamino, cyclobutylamino, cyclopentylamino, cyclohexylamino, benzylamino, cyanomethyl, cyanoethyl, 3-cyanoprop-1-yl, 2cyanoprop-l-yl, 1-cyanoprop-1-yl, 2-cyanoprop-2-yl, 2-cyano-l,l-dimethyleth-l-yl, 1(cyanomethyl)-1 -methylprop-1 -yl, hydroxycarbonyl, hydroxycarbonylmethyl, hydroxycarbonylethyl, CHO, methoxyethylthio, ethoxyethylthio, trifluoromethoxyethylthio, pentafluoroethoxyethylthio, methylthioethylthio, ethylthioethylthio, trifhioromethylthioethylthio, pentafluorothioethylthio, benzylthio, pchlorophenylmethylthio, m-chlorophenylmethylthio, o-chlorophenylmethylthio, pfluorophenylmethylthio, m-fluorophenylmethylthio, o-fluorophenylmethylthio, methylthio, ethylthio, n-propylthio, isopropylthio, n-butylthio, tert-butylthio, cyclobutylthio, cyclopentylthio, cyclohexylthio, phenylthio, pyrid-2-ylthio, pyrid-3ylthio, pyrid-4-ylthio, p-chlorophenylthio, m-chlorophenylthio, o-chlorophenylthio, pfluorophenylthio, m-fluorophenylthio, o-fluorophenylthio, p-methoxyphenylthio, mmethoxyphenylthio, o-methoxyphenylthio, p-methylphenylthio, m-methylphenylthio, omethylphenylthio, methylsulfonyl, ethylsulfonyl, n-propylsulfonyl, 1 methylethylsulfonyl, cyclopropylsulfonyl, cyclobutylsulfonyl, cyclopentylsulfonyl, cyclohexylsulfonyl, phenylsulfonyloxy, p-chlorophenylsulfonyl, mchlorophenylsulfonyl, o-chlorophenylsulfonyl, p-fluorophenylsulfonyl, mfluorophenylsulfonyl, o-fluorophenylsulfonyl, p-methoxyphenylsulfonyl, mmethoxyphenylsulfonyl, o-methoxyphenylsulfonyl, p-methylphenylsulfonyl, mmethylphenylsulfonyl, o-methylphenylsulfonyl, 2-methoxyprop-2-yl, 2-ethoxyprop-2-yl, 2-n-propyloxyprop-2-yl, 2-n-butyloxyprop-2-yl, 2-benzyloxyprop-2-yl, 2phenylethyloxyprop-2-yl, 2-trifluoromethyloxyprop-2-yl, 2-difluoromethyloxyprop-2-yl,
    2,2,2-trifluoroethyloxyprop-2-yl, 2,2-difluoroethyloxyprop-2-yl, 2-(4chlorophenylmethoxy)prop-2-yl, 2-(4-fluorophenylmethoxy)prop-2-yl, 2-(4bromophenylmethoxy)prop-2-yl, 2-(4-trifluoromethylphenylmethoxy)prop-2-yl, 2-(4methylphenylmethoxy)prop-2-yl, 2-(3-chlorophenylmethoxy)prop-2-yl, 2-(3fluorophenylmethoxy)prop-2-yl, 2-(3-bromophenylmethoxy)prop-2-yl, 2-(3trifluoromethylphenylmethoxy)prop-2-yl, 2-(3-methylphenylmethoxy)prop-2-yl, 2-(2chlorophenylmethoxy)prop-2-yl, 2-(2-fluorophenylmethoxy)prop-2-yl, 2-(2bromophenylmethoxy)prop-2-yl, 2-(2-trifluoromethylphenylmethoxy)prop-2-yl, 2-(2methylphenylmethoxy)prop-2-yl, 2-(methoxymethyl)prop-2-yl, 2-(ethoxymethyl)prop2-yl, 2-methoxycarbonylprop-2-yl, 2-ethoxycarbonylprop-2-yl, 2-hydroxycarbonylprop2-yl, 2-aminocarbonylprop-2-yl, aminocarbonyl, aminocarbonylmethyl,
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    221 aminocarbonylethyl, cyano, hydroxymethyl, hydroxyethyl, 2-hydroxyprop-2-yl, allyloxymethyl, 2-allyloxyethyl, 2-allyloxyprop-2-yl, or where R4 and R7 together with the carbon atom to which they are respectively attached form a partially saturated ring having a total of 3 to 7 members which is optionally interrupted by one to three heteroatoms from the group consisting of N, O and S and optionally substituted further, if Q represents Q-3, Q-4, Q-8, Q-9, Q-12 or Q-19,
    R5 represents hydrogen, formyl, methyl, ethyl, n-propyl, 1 -methylethyl, n-butyl, 1 methylpropyl, 2-methylpropyl, 1,1 -dimethylethyl, n-pentyl, 1 -methylbutyl, 2methylbutyl, 3-methylbutyl, 1,1-dimethylpropyl, 1,2-dimethylpropyl, 2,2dimethylpropyl, 1-ethylpropyl, n-hexyl, 1-methylpentyl, 2-methylpentyl, 3methylpentyl, 4-methylpentyl, 1,1-dimethylbutyl, 1,2-dimethylbutyl, 1,3-dimethylbutyl,
    2.2- dimethylbutyl, 2,3-dimethylbutyl, 3,3-dimethylbutyl, 1-ethylbutyl, 2-ethylbutyl,
    1.1.2- ttimethylpropyl, 1,2,2-ttimethylpropyl, 1 -ethyl-1 -methylpropyl, 1 -ethyl-2methylpropyl, 2,2-difluoroethyl, 2,2,2-trifluoroethyl, 3,3,3-ttifluoro-n-propyl, methoxymethyl, ethoxymethyl, methoxyethyl, ethoxyethyl, methoxy-n-propyl, methoxy-n-butyl, ethoxy-n-propyl, ethoxy-n-butyl, hydroxyethyl, hydroxy-n-propyl, hydroxycarbonylmethyl, hydroxycarbonylethyl, hydroxycarbonyl-n-propyl, methoxycarbonylmethyl, ethoxycarbonylmethyl, n-propyloxycarbonylmethyl, isopropyloxycarbonylmethyl, tert-butyloxycarbonylmethyl, methoxycarbonylethyl, ethoxycarbonylethyl, n-propyloxycarbonylethyl, isopropyloxycarbonylethyl, tertbutyloxycarbonylethyl, methoxycarbonyl-n-propyl, ethoxycarbonyl-n-propyl, benzyloxycarbonylmethyl, benzyloxycarbonylethyl, allyloxycarbonylmethyl, allyloxycarbonylethyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, 1methylcycloprop-1-yl, 2-methylcycloprop-1-yl, 2,2-dimethylcycloprop-l-yl, 2,3dimethylcyclopropyl, 1-cyanopropyl, 2-cyanopropyl, 1-methylcyclobutyl, 2methylcyclobutyl, 3-methylcyclobutyl, 3,3-dimethylcyclobutyl, 1-cyanocyclobutyl, 2cyanocyclobutyl, 3-cyanocyclobutyl, 1-allylcyclopropyl, 1-vinylcyclobutyl, 1vinylcyclopropyl, 1-ethylcyclopropyl, 1-methylcyclohexyl, 2-methylcyclohexyl, 3methylcyclohexyl, 1-methoxycyclohexyl, 2-methoxycyclohexyl, 3-methoxycyclohexyl, cyclopropylmethyl, cyclobutylmethyl, cyclopentylmethyl, cyclohexylmethyl, cyanomethyl, 2-cyanoeth-l-yl, l-cyanoeth-l-yl, cyano-n-propyl, methoxycarbonyl, ethoxycarbonyl, tert-butyloxycarbonyl, benzyloxycarbonyl, n-butyloxycarbonyl, allyloxycarbonyl, methylcarbonyl, ethylcarbonyl, n-propylcarbonyl, isopropylcarbonyl, n-butylcarbonyl, tert-butylcarbonyl, phenylcarbonyl, p-chlorophenylcarbonyl, m
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    222 chlorophenylcarbonyl, o-chlorophenylcarbonyl, p-fluorophenylcarbonyl, mfluorophenylcarbonyl, o-fluorophenylcarbonyl, p-methoxyphenylcarbonyl, mmethoxyphenylcarbonyl, o-methoxyphenylcarbonyl, p-trifluoromethylphenylcarbonyl, m-trifluoromethylphenylcarbonyl, o-trifluoromethylphenylcarbonyl, methylaminocarbonyl, ethylaminocarbonyl, isopropylaminocarbonyl, npropylaminocarbonyl, phenylaminocarbonyl, p-Clphenylaminocarbonyl, mClphenylaminocarbonyl, o-Clphenylaminocarbonyl, cyclopropylaminocarbonyl, cyclobutylaminocarbonyl, cyclopentylaminocarbonyl, cyclohexylaminocarbonyl, cyclopropylmethylaminocarbonyl, cyclobutylmethylaminocarbonyl, cyclopentylmethylaminocarbonyl, cyclohexylmethylaminocarbonyl, dimethylaminocarbonyl, diethylaminocarbonyl, benzyl(methyl)aminocarbonyl, prop -2 en-l-yl, prop-2-yn-l-yl, 1-fluorocycloprop-1-yl, 2-fluorocycloprop-1-yl, 2,2difluorocycloprop-l-yl, 3,3-difluorocyclobut-l-yl, phenyl, 2-fluorophenyl, 3fluorophenyl, 4-fluorophenyl, 2,4-difluorophenyl, 2,5-difluorophenyl, 2,6difluorophenyl, 2,3-difluorophenyl, 3,4-difluorophenyl, 3,5-difluorophenyl, 2,4,5trifluorophenyl, 3,4,5-trifluorophenyl, 2-chlorophenyl, 3-chlorophenyl, 4-chlorophenyl,
    2.4- dichlorophenyl, 2,5-dichlorophenyl, 2,6-dichlorophenyl, 2,3-dichlorophenyl, 3,4dichlorophenyl, 3,5-dichlorophenyl, 2,4,5-trichlorophenyl, 3,4,5-trichlorophenyl, 2,4,6trichlorophenyl, 2-bromophenyl, 3-bromophenyl, 4-bromophenyl, 2-iodophenyl, 3iodophenyl, 4-iodophenyl, 2-bromo-4-fluorophenyl, 2-bromo-4-chlorophenyl, 3-bromo-
    4-fluorophenyl, 3-bromo-4-chlorophenyl, 3-bromo-5-fluorophenyl, 3-bromo-5chlorophenyl, 2-fluoro-4-bromophenyl, 2-chloro-4-bromophenyl, 3-fluoro-4bromophenyl, 3-chloro-4-bromophenyl, 2-chloro-4-fluorophenyl, 3-chloro-4fluorophenyl, 2-fluoro-3-chlorophenyl, 2-fluoro-4-chlorophenyl, 2-fluoro-5chlorophenyl, 3-fluoro-4-chlorophenyl, 3-fluoro-5-chlorophenyl, 2-fluoro-6chlorophenyl, 2-methylphenyl, 3-methylphenyl, 4-methylphenyl, 2,4-dimethylphenyl,
    2.5- dimethylphenyl, 2,6-dimethylphenyl, 2,3-dimethylphenyl, 3,4-dimethylphenyl, 3,5dimethylphenyl, 2,4,5-trimethylphenyl, 3,4,5-trimethylphenyl, 2,4,6-trimethylphenyl, 2methoxyphenyl, 3-methoxyphenyl, 4-methoxyphenyl, 2,4-dimethoxyphenyl, 2,5dimethoxyphenyl, 2,6-dimethoxyphenyl, 2,3-dimethoxyphenyl, 3,4-dimethoxyphenyl,
    3.5- dimethoxyphenyl, 2,4,5-trimethoxyphenyl, 3,4,5-trimethoxyphenyl, 2,4,6trimeflioxyphenyl, 2-trifluoromethoxyphenyl, 3-trifluoromethoxyphenyl, 4trifluoromethoxyphenyl, 2-difluoromethoxyphenyl, 3-difluoromethoxyphenyl, 4difluoromethoxyphenyl, 2-trifluoromethylphenyl, 3-trifluoromethylphenyl, 4trifluoromethylphenyl, 2-difluoromethylphenyl, 3-difluoromethylphenyl, 4difluoromethylphenyl, 3,5-bis(trifluoromethyl)phenyl, 3-trifluoromethyl-5-fluorophenyl, 3 -trifluoromethyl-5 -chlorophenyl, 3 -methyl-5-fluorophenyl, 3 -methyl-5-chlorophenyl,
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    3 -methoxy-5-fluorophenyl, 3 -methoxy-5 -chlorophenyl, 3 -trifluoromethoxy-5chlorophenyl, 2-ethoxyphenyl, 3-ethoxyphenyl, 4-ethoxyphenyl, 2-methyhhiophenyl, 3methylthiophenyl, 4-methylthiophenyl, 2-trifluoromethyhhiophenyl, 3trifluoromethyhhiophenyl, 4-trifluoromethyhhiophenyl, methoxymethyl, 2-ethylphenyl,
    3-ethylphenyl, 4-ethylphenyl, 2-methoxycarbonylphenyl, 3-methoxycarbonylphenyl, 4methoxycarbonylphenyl, 2-ethoxycarbonylphenyl, 3-ethoxycarbonylphenyl, 4ethoxycarbonylphenyl, pyridin-2-yl, pyridin-3-yl, pyridin-4-yl, pyrazin-2-yl, pyridazin3-yl, pyridazin-4-yl, pyrimidin-2-yl, pyrimidin-5-yl, pyrimidin-4-yl, pyridazin-3ylmethyl, pyridazin-4-ylmethyl, pyrimidin-2-ylmethyl, pyrimidin-5-ylmethyl, pyrimidin-4-ylmethyl, pyrazin-2-ylmethyl, 3-chloro-pyrazin-2-yl, 3-bromo-pyrazin-2-yl, 3-methoxy-pyrazin-2-yl, 3-ethoxy-pyrazin-2-yl, 3-trifluoromethylpyrazin-2-yl, 3cyanopyrazin-2-yl, naphth-2-yl, naphth-1-yl, quinolin-4-yl, quinolin-6-yl, quinolin-8-yl, quinolin-2-yl, quinoxalin-2-yl, 2-naphthylmethyl, 1-naphthylmethyl, quinolin-4ylmethyl, quinolin-6-ylmethyl, quinolin-8-ylmethyl, quinolin-2-ylmethyl, quinoxalin-2ylmethyl, pyrazin-2-ylmethyl, 4-chloropyridin-2-yl, 3-chloropyridin-4-yl, 2chloropyridin-3-yl, 2-chloropyridin-4-yl, 2-chloropyridin-5-yl, 2,6-dichloropyridin-4-yl, 3 -chloropyridin-5-yl, 3,5 -dichloropyridin-2-yl, 3 -chloro-5-trifluoromethylpyridin-2-yl, (4-chloropyridin-2-yl)methyl, (3-chloropyridin-4-yl)methyl, (2-chloropyridin-3yl)methyl, (2-chloropyridin-4-yl)methyl, (2-chloropyridin-5-yl)methyl, (2,6dichloropyridin-4-yl)methyl, (3-chloropyridin-5-yl)methyl, (3,5-dichloropyridin-2yl)methyl, thiophen-2-yl, thiophen-3-yl, 5-methylthiophen-2-yl, 5-ethylthiophen-2-yl, 5chlorothiophen-2-yl, 5-bromothiophen-2-yl, 4-methylthiophen-2-yl, 3-methyhhiophen2-yl, 5-fluorothiophen-3-yl, 3,5-dimethylthiophen-2-yl, 3-ethylthiophen-2-yl, 4,5dimethylthiophen-2-yl, 3,4-dimethylthiophen-2-yl, 4-chlorothiophen-2-yl, furan-2-yl, 5methylfuran-2-yl, 5-ethylfuran-2-yl, 5-methoxycarbonylfuran-2-yl, 5-chlorofuran-2-yl,
    5-bromofuran-2-yl, thiophan-2-yl, thiophan-3-yl, sulfolan-2-yl, sulfolan-3-yl, benzyl, (4fluorophenyl)methyl, (3-fluorophenyl)methyl, (2-fluorophenyl)methyl, (2,4difluorophenyl)methyl, (3,5-difluorophenyl)methyl, (2,5-difluorophenyl)methyl, (2,6difluorophenyl)methyl, (2,4,5-trifluorophenyl)methyl, (2,4,6-trifluorophenyl)methyl, (4chlorophenyl)methyl, (3-chlorophenyl)methyl, (2-chlorophenyl)methyl, (2,4dichlorophenyl)methyl, (3,5-dichlorophenyl)methyl, (2,5-dichlorophenyl)methyl, (2,6dichlorophenyl)methyl, (2,4,5-trichlorophenyl)methyl, (2,4,6-trichlorophenyl)methyl, (4-bromophenyl)methyl, (3-bromophenyl)methyl, (2-bromophenyl)methyl, (4iodophenyl)methyl, (3-iodophenyl)methyl, (2-iodophenyl)methyl, (3-chloro-5trifluoromethyl-pyridin-2-yl)methyl, (2-bromo-4-fluorophenyl)methyl, (2-bromo-4chlorophenyl)methyl, (3-bromo-4-fluorophenyl)methyl, (3-bromo-4chlorophenyl)methyl, (3-bromo-5-fluorophenyl)methyl, (3-bromo-5WO 2018/114596
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    224 chlorophenyl)methyl, (2-fluoro-4-bromophenyl)methyl, (2-chloro-4bromophenyl)methyl, (3-fluoro-4-bromophenyl)methyl, (3-chloro-4bromophenyl)methyl, (2-chloro-4-fluorophenyl)methyl, (3-chloro-4fluorophenyl)methyl, (2-fluoro-3-chlorophenyl)methyl, (2-fluoro-4chlorophenyl)methyl, (2-fluoro-5-chlorophenyl)methyl, (3-fluoro-4chlorophenyl)methyl, (3-fluoro-5-chlorophenyl)methyl, (2-fluoro-6chlorophenyl)methyl, phenylethyl, 3-trifluoromethyl-4-chlorophenyl, 3-chloro-4trifluoromethylphenyl, 2-chloro-4-trifluoromethylphenyl, 3,5-difluoropyridin-2-yl, (3,6dichloropyridin-2-yl)methyl, (4-trifluoromethylphenyl)methyl, (3trifluoromethylphenyl)methyl, (2-trifluoromethylphenyl)methyl, (4trifluoromethoxyphenyl)methyl, (3-trifluoromethoxyp henyl)methyl, (2trifluoromethoxyphenyl)methyl, (4-methoxyphenyl)methyl, (3 -methoxyphenyl)methyl, (2-methoxyphenyl)methyl, (4-methylphenyl)methyl, (3-methylphenyl)methyl, (2methylphenyl)methyl, (4-cyanophenyl)methyl, (3-cyanophenyl)methyl, (2cyanophenyl)methyl, (2,4-diethylphenyl)methyl, (3,5-diethylphenyl)methyl, (3,4dimethylphenyl)methyl, (3,5-dimethoxyphenyl)methyl, 1 -phenyleth-1 -yl, methylsulfonyl, ethylsulfonyl, n-propylsulfonyl, 1 -methylethylsulfonyl, cyclopropylsulfonyl, cyclobutylsulfonyl, cyclopentylsulfonyl, cyclohexylsulfonyl, phenylsulfonyloxy, p-chlorophenylsulfonyl, m-chlorophenylsulfonyl, ochlorophenylsulfonyl, p-fluorophenylsulfonyl, m-fluorophenylsulfonyl, ofluorophenylsulfonyl, p-methoxyphenylsulfonyl, m-methoxyphenylsulfonyl, omethoxyphenylsulfonyl, p-methylphenylsulfonyl, m-methylphenylsulfonyl, omethylphenylsulfonyl, phenylcarbonylmethyl, p-chlorophenylcarbonylmethyl, mchlorophenylcarbonylmethyl, o-chlorophenylcarbonylmethyl, pfluorophenylcarbonylmethyl, m-fluorophenylcarbonylmethyl, ofluorophenylcarbonylmethyl, methylcarbonylmethyl, ethylcarbonylmethyl, npropylcarbonylmethyl, isopropylcarbonylmethyl, n-butylcarbonylmethyl, tertbutylcarbonylmethyl, or where R4 and R5 together with the nitrogen atom or carbon atom to which they are respectively attached form a partially saturated ring having a total of 3 to 7 members which is optionally interrupted by one to three heteroatoms from the group consisting of N, O and S and optionally substituted further, if Q represents Q-13, Q-14 or Q-15,
    R6 represents hydrogen, methyl, ethyl,
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    R8 represents hydrogen, halogen, cyano, nitro, hydrothio, hydroxy, methylamino, ethylamino, isopropylamino, n-propylamino, dimethylamino, diethylamino, cyclopropylamino, cyclobutylamino, cyclopentylamino, cyclohexylamino, methoxycarbonylmethylamino, methoxycarbonylethylamino, ethoxycarbonylmethylamino, ethoxycarbonylethylamino, methoxycarbonylamino, ethoxycarbonylamino, tert-butyloxycarbonylamino, phenylamino, N-piperidinyl, Npyrrolidinyl, N-morpholinyl, methylaminocarbonylamino, ethylaminocarbonylamino, npropylaminocarbonylamino, isopropylaminocarbonylamino, benzylaminocarbonylamino, phenylaminocarbonylamino, pClphenylaminocarbonylamino, m-Clphenylaminocarbonylamino, oClphenylaminocarbonylamino, cyclopropylaminocarbonylamino, cyclobutylaminocarbonylamino, cyclopentylaminocarbonylamino, cyclohexylaminocarbonylamino, dimethylaminocarbonylamino, methoxy, ethoxy, npropyloxy, isopropyloxy, n-butyloxy, tert-butyloxy, methoxy carbonyloxy, ethoxy carbonyloxy, tert-butyloxycarbonyloxy, methylaminocarbonyloxy, ethylaminocarbonyloxy, n-propylaminocarbonyloxy, isopropylaminocarbonyloxy, benzylaminocarbonyloxy, phenylaminocarbonyloxy, cyclopropylaminocarbonyloxy, cyclobutylaminocarbonyloxy, cyclopentylaminocarbonyloxy, cyclohexylaminocarbonyloxy, dimethylaminocarbonyloxy, phenyloxy, p-Clphenyloxy, o-Clphenyloxy, m-Clphenyloxy, m-trifluoromethylphenyloxy, ptrifluoromethylphenyloxy, trifluoromethyloxy, difluoromethyloxy, 2,2-difluoroethyloxy,
    2,2,2-trifluoroethyloxy, methylthio, ethylthio, n-propylthio, isopropylthio, phenylthio, pClphenylthio, m-Clphenylthio, o-Clphenylthio, pyridin-2-ylthio, pyridin-3-yhhio, benzylthio, trifluoromethylthio, pentafluoroethylthio, cyclopropylthio, cyclobutylthio, cyclopentylthio, cyclohexylthio, methylsulfinyl, ethylsulfinyl, n-propylsulfinyl, isopropylsulfinyl, n-butylsulfinyl, tert-butylsulfinyl, phenylsulfinyl, benzylsulfinyl, pyridin-2-ylsulfinyl, methylsulfonyl, ethylsulfonyl, n-propylsulfonyl, isopropylsulfonyl, n-butylsulfonyl, tert-butylsulfonyl, phenylsulfonyl, benzylsulfonyl, pyridin-2-ylsulfonyl, methyl, ethyl, n-propyl, 1 -methylethyl, n-butyl, 1 -methylpropyl, 2-methylpropyl, 1,1dimethylethyl, n-pentyl, 1-methylbutyl, 2-methylbutyl, 3-methylbutyl, 1,1dimethylpropyl, 1,2-dimethylpropyl, 2,2-dimethylpropyl, 1 -ethylpropyl, n-hexyl, 1 methylpentyl, 2-methylpentyl, 3-methylpentyl, 4-methylpentyl, 1,1-dimethylbutyl, 1,2dimethylbutyl, 1,3-dimethylbutyl, 2,2-dimethylbutyl, 2,3-dimethylbutyl, 3,3dimethylbutyl, 1 -ethylbutyl, 2-ethylbutyl, 1,1,2-trimethylpropyl, 1,2,2-trimethylpropyl, 1 -ethyl-1 -methylpropyl, 1 -ethyl-2-methylpropyl, thiocyanate, isothiocyanate, formyl, ethenyl, 1-propenyl, 2-propenyl, 1-methylethenyl, l-butenyl, 2-butenyl, 3-butenyl, 1methyl-l-propenyl, 2-methyl-l-propenyl, l-methyl-2-propenyl, 2-methyl-2-propenyl, 1
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    226 pentenyl, 2-pentenyl, 3-pentenyl, 4-pentenyl, 1-methyl-l-butenyl, 2-methyl-l-butenyl, 3-methyl-l-butenyl, 1-methyl-2-butenyl, 2-methyl-2-butenyl, 3-methyl-2-butenyl, 1methyl-3-butenyl, 2-methyl-3-butenyl, 3-methyl-3-butenyl, 1,1-dimethyl-2-propenyl,
    1,2-dimethyl-1-propenyl, 1,2-dimethyl-2-propenyl, 1-ethyl-1-propenyl, 1-ethyl-2propenyl, ethynyl, 1-propynyl, 2-propynyl, l-butynyl, 2-butynyl, 3-butynyl, 1-methyl-2propynyl, 1-pentynyl, 2-pentynyl, 3-pentynyl, 4-pentynyl, 1-methyl-2-butynyl, 1methyl-3-butynyl, 2-methyl-3-butynyl, 3-methyl-l-butynyl, l,l-dimethyl-2-propynyl, 1ethyl-2-propynyl, 1-hexynyl, 2-hexynyl, 3-hexynyl, 3,3-difluorcyclobut-l-yl, 3fluorocyclobut-1 -yl, 1 -fluorocyclobut-1 -yl, 2,2-difluorocycloprop-1 -yl, 1 fluorocycloprop-1-yl, 2-fluorocycloprop-1 -yl, 4-fluorocyclohexyl, 4,4difluorocyclohexyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, 1methylcycloprop-1-yl, 2-methylcycloprop-1-yl, 2,2-dimethylcycloprop-l-yl, 2,3dimethylcyclopropyl, 1-cyanopropyl, 2-cyanopropyl, 1-methylcyclobutyl, 2methylcyclobutyl, 3-methylcyclobutyl, 3,3-dimethylcyclobutyl, 1-cyanocyclobutyl, 2cyanocyclobutyl, 3-cyanocyclobutyl, 1-allylcyclopropyl, 1-vinylcyclobutyl, 1vinylcyclopropyl, 1-ethylcyclopropyl, 1-methylcyclohexyl, 2-methylcyclohexyl, 3methylcyclohexyl, 1-methoxycyclohexyl, 2-methoxycyclohexyl, 3-methoxycyclohexyl, spiro[2.2]pent-l-yl, spiro[2.3]hex-l-yl, spiro[2.3]hex-4-yl, 3-spiro[2.3]hex-5-yl, spiro[3.3]hept-l-yl, spiro[3.3]hept-2-yl, bicyclo[1.1.0]butan-l-yl, bicyclo[1.1.0]butan-2yl, bicyclo[2.1.0]pentan-l-yl, bicyclo[l.l.l]pentan-l-yl, bicyclo[2.1.0]pentan-2-yl, bicyclo[2.1,0]pentan-5-yl, bicyclo[2.1. l]hexyl, bicyclo[2.2. l]hept-2-yl, bicyclo[2.2.2]octan-2-yl, bicyclo[3.2.1]octan-2-yl, bicyclo[3.2.2]nonan-2-yl, adamantan-1 -yl, adamantan-2-yl, cyclopropylmethyl, cyclobutylmethyl, cyclopentylmethyl, cyclohexylmethyl, trifluoromethyl, pentafluoroethyl, 1,1,2,2tetrafluoroethyl, heptafluoro-n-propyl, heptafluoroisopropyl, nonafluorobutyl, chlorodifluoromethyl, bromodifluoromethyl, dichlorofluoromethyl, iododifluoromethyl, bromo fluoromethyl, 1 -fluoroethyl, 2-fluoroethyl, fluoromethyl, difluoromethyl, 2,2difluoroethyl, 2,2,2-trifluoroethyl, difluoro-tert-butyl, chloromethyl, bromomethyl, fluoromethyl, 3,3,3-trifluoro-n-propyl, methoxycarbonyl, ethoxycarbonyl, isopropyloxycarbonyl, n-propyloxycarbonyl, n-butyloxycarbonyl, tert-butyloxycarbonyl, benzyloxycarbonyl, allyloxycarbonyl, methylaminocarbonyl, ethylaminocarbonyl, npropylaminocarbonyl, isopropylaminocarbonyl, benzylaminocarbonyl, phenylaminocarbonyl, cyclopropylaminocarbonyl, cyclobutylaminocarbonyl, cyclopentylaminocarbonyl, cyclohexylaminocarbonyl, dimethylaminocarbonyl, diethylaminocarbonyl, allylaminocarbonyl, pentafluorothio, methoxydifluoromethyl, ethoxydifluoromethyl, n-propyloxydifluoromethyl, trifluoromethoxymethyl, trifluoromethoxyethyl, trifluoromethoxy-n-propyl, methoxymethyl, ethoxymethyl, n
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    227 propyloxymethyl, ethoxyethyl, methoxyethyl, n-propyloxyethyl, methoxy-n-propyl, ethoxy-n-propyl, 1-methoxyeth-1-yl, 1-methoxyprop-1-yl, l-ethoxyeth-l-yl, 2methoxyprop-2-yl, 2-ethoxyprop-2-yl, methylthiomethyl, methylthioethyl, methylthio-npropyl, ethylthiomethyl, trifluoromethylthiomethyl, petntafluoroethylthiomethyl, trifluoromethyhhioethyl, trifluoromethylthio-n-propyl, methylcarbonyl, ethylcarbonyl, isopropylcarbonyl, n-butylcarbonyl, tert-butylcarbonyl, phenylcarbonyl, oClphenylcarbonyl, m-Clphenylcarbonyl, p-Clphenylcarbonyl, methoxycarbonylmethyl, ethoxycarbonylmethyl, methoxycarbonylethyl, ethoxycarbonylethyl, npropyloxycarbonylmethyl, tert-butyloxycarbonylmethyl, tert-butyloxycarbonylethyl, hydroxycarbonylmethyl, hydroxycarbonylethyl, hydroxycarbonyl, methylaminocarbonylmethyl, ethylaminocarbonylmethyl, npropylaminocarbonylmethyl, isopropylaminocarbonylmethyl, benzylaminocarbonylmethyl, phenylaminocarbonylmethyl, cyclopropylaminocarbonylmethyl, cyclobutylaminocarbonylmethyl, cyclopentylaminocarbonylmethyl, cyclohexylaminocarbonylmethyl, dimethylaminocarbonylmethyl, diethylaminocarbonylmethyl, allylaminocarbonylmethyl, methylaminomethyl, dimethylaminomethyl, diethylaminomethyl, ethylaminomethyl, isopropylaminomethyl, n-propylaminomethyl, n-butylaminomethyl, methylaminoethyl, dimethylaminoethyl, diethylaminoethyl, Npyrrolidinylmethyl, N-piperidinylmethyl, hydroxyimino, methoxyimino, ethoxyimino, n-propyloxyimino, n-butyloxyimino, isopropyloxyimino, tert-butyloxyimino, cyclopropylmethoxyimino, cyclobutylmethoxyimino,cyclopentylmethoxyimino, cyclohexylmethoxyimino, benzyloxyimino, phenyloxyimino, allyloxyimino, pClphenylmethyloxyimino, phenylethynyl, p-Clphenylethynyl, m-Clphenylethynyl, oClphenylethynyl, p-F-phenylethynyl, m-F-phenylethynyl, o-F-phenylethynyl, pyridin-2ylethynyl, pyridin-3-ylethynyl, thiophen-2-ylethynyl, trimethylsilylethynyl, triethylsilylethynyl, tri(isopropyl)silylethynyl, cyclopropylethynyl, cyclobutylethynyl, cyclopentylethynyl, cyclohexylethynyl, phenyl, benzyl, p-Clphenyl, m-Clphenyl, oClphenyl, p-F-phenyl, m-F-phenyl, o-F-phenyl, p-trifluoromethylphenyl, mtrifluoromethylphenyl, o-trifluoromethylphenyl, p-methylphenyl, m-methylphenyl, omethylphenyl, p-methoxyphenyl, m-methoxyphenyl, o-methoxyphenyl, pClphenylmethyl, m-Clphenylmethyl, o-Clphenylmethyl, pyridin-2-yl, pyridin-3-yl, pyridin-4-yl, thiophen-2-yl, thiophen-3-yl, furan-2-yl, furan-3-yl, pyrimidin-2-yl, pyrazin-2-yl, methoxymethoxymethyl, ethoxy ethoxymethyl, methoxy ethoxymethyl, methylaminosulfonylamino, dimethylaminosulfonylamino, ethylaminosulfonylamino, diethylaminosulfonylamino, isopropylaminosulfonylamino, cyclopropylaminosulfonylamino, cyclobutylaminosulfonylamino,
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    228 cyclopentylaminosulfonylamino, cyclohexylaminosulfonylamino, diazo, phenyldiazo, trimethylsilyl, tri(isopropyl)silyl, triethylsilyl, dimethyl(phenyl)silyl, diphenyl(methyl) silyl, or where A1 and A2, when each is a group C-R8, together with the atoms to which they are attached form a partially saturated or fully unsaturated 5- to 7-membered ring which is optionally interrupted by heteroatoms from the group consisting of N, O and S and optionally substituted further, or where A2 and A3, when each is a group C-R8, together with the atoms to which they are attached form a partially saturated or fully unsaturated 5- to 7-membered ring which is optionally interrupted by heteroatoms from the group consisting of N, O and S and optionally substituted further, or where A3 and A4, when each is a group C-R8, together with the atoms to which they are attached form a partially saturated or fully unsaturated 5- to 7-membered ring which is optionally interrupted by heteroatoms from the group consisting of N, O and S and optionally substituted further and
    W represents oxygen.
    5. The compound of the general formula (1) as claimed in claim 1 and/or the salt thereof, characterized in that
    X and Y independently of one another represent C-H or the moiety C-R1, where
    X represents C-H if Y represents the moiety C-R1 and
    X represents the moiety C-R1 if Y represents C-H,
    R1 represents chlorine, bromine, iodine, methyl, ethyl, n-propyl, 1 -methylethyl, n-butyl, 1 methylpropyl, 2-methylpropyl, 1,1 -dimethylethyl, n-pentyl, 1 -methylbutyl, 2methylbutyl, 3-methylbutyl, 1,1-dimethylpropyl, 1,2-dimethylpropyl, 2,2dimethylpropyl, 1-ethylpropyl, n-hexyl, 1-methylpentyl, 2-methylpentyl, 3methylpentyl, 4-methylpentyl, 1,1-dimethylbutyl, 1,2-dimethylbutyl, 1,3-dimethylbutyl,
    2.2- dimethylbutyl, 2,3-dimethylbutyl, 3,3-dimethylbutyl, 1-ethylbutyl, 2-ethylbutyl,
    1.1.2- trimethylpropyl, 1,2,2-trimethylpropyl, 1-ethyl-1-methylpropyl, 1-ethyl-2
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    229 methylpropyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, adamantan-l-yl, adamantan-2-yl, 1-methylcyclopropyl, 2-methylcyclopropyl, 2,2-dimethylcyclopropyl, 2,3-dimethylcyclopropyl, l,l'-bi(cyclopropyl)-l-yl, l,l'-bi(cyclopropyl)-2-yl, 2'-methyl1,1 '-bi(cyclopropyl)-2-yl, 1 -cyanocyclopropyl, 2-cyanocyclopropyl, 1 -methylcyclobutyl, 2-methylcyclobutyl, 3-methylcyclobutyl, 3,3-dimethylcyclobut-l-yl, 3,3difluorocyclobut-l-yl, 3-fluorocyclobut-l-yl, 2,2-difluorocycloprop-1 -yl, 1fluorocycloprop-l-yl, 2-fluorocycloprop-1 -yl, 1-ethylcyclopropyl, 1-methylcyclohexyl,
    2- methylcyclohexyl, 3-methylcyclohexyl, 1-methoxycyclohexyl, 2-methoxycyclohexyl,
    3- methoxycyclohexyl, trifluoromethyl, pentafluoroethyl, 1,1,2,2-tetrafluoroethyl, heptafluoropropyl, nonafluorobutyl, chlorodifluoromethyl, difluoromethyl, 2,2difluoroethyl, 2,2,2-trifluoroethyl, difluoro-tert-butyl, methoxy, ethoxy, n-propyloxy, isopropyloxy, n-butyloxy, tert-butyloxy, methoxymethyl, ethoxymethyl, methoxyethyl, ethoxyethyl, trifluoromethoxy, difluoromethoxy, 2,2,2-trifluoroethoxy, 2,2difluoroethoxy, methylthio, ethylthio, trifluoromethylthio, pentafluoroethylthio, phenyl, phenyloxy, p-Clphenyloxy, thiophen-2-yl, thiophen-3-yl, pyridin-2-yl, pyridin-3-yl, pyridin-4-yl, furan-2-yl, furan-3-yl, cyclopropylmethyl, cyclobutylmethyl, cyclopentylmethyl, cyclohexylmethyl, ethenyl, 1-propenyl, 2-propenyl, 1methylethenyl, l-butenyl, 2-butenyl, 3-butenyl, 1-methyl-1-propenyl, 2-methyl-1propenyl, 1-methyl-2-propenyl, 2-methyl-2-propenyl, l-pentenyl, 2-pentenyl, 3pentenyl, 4-pentenyl, prop-2-en-l-yloxy, but-3-en-l-yloxy, pent-4-en-l-yloxy, ethynyl,
    1- propynyl, 2-propynyl, l-butynyl, 1-pentynyl, 1-hexynyl, 2-(trimethylsilyl)ethyn-l-yl,
    2- (triethylsilyl)ethyn-l-yl, 2-(triisopropylsilyl)ethyn-l-yl, amino, methylamino, ethylamino, dimethylamino, diethylamino,
    R3 represents hydroxy, methoxy, ethoxy, n-propyloxy, 1 -methylethoxy, n-butyloxy, 1 methylpropyloxy, 2-methylpropyloxy, 1,1 -dimethylethoxy, n-pentyloxy, cyclopropylmethoxy, cyclobutylmethoxy, cyclopentylmethoxy, cyclohexylmethoxy, benzyloxy, p-chlorophenylmethoxy, m-chlorophenylmethoxy, o-chlorophenylmethoxy, p-methoxyphenylmethoxy, methoxymethoxy, methoxyethoxy, methoxy-n-propyloxy, ethoxymethoxy, ethoxyethoxy, methylcarbonyloxy, ethylcarbonyloxy, npropylcarbonyloxy, 1-methylethylcarbonyloxy, n-butylcarbonyloxy, 1methylpropylcarbonyloxy, 2-methylpropylcarbonyloxy, 1,1 -dimethylethylcarbonyloxy, n-pentylcarbonyloxy, phenylcarbonyloxy, p-chlorophenylcarbonyloxy, mchlorophenylcarbonyloxy, o-chlorophenylcarbonyloxy, p-fluorophenylcarbonyloxy, mfluorophenylcarbonyloxy, o-fluorophenylcarbonyloxy, cyclopropylcarbonyloxy, cyclobutylcarbonyloxy, cyclopentylcarbonyloxy, cyclohexylcarbonyloxy, trifluoromethylcarbonyloxy, difluoromethylcarbonyloxy, methoxycarbonyloxy,
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    230 ethoxycarbonyloxy, n-propyloxycarbonyloxy, isopropyloxycarbonyloxy, nbutyloxycarbonyloxy, 1,1-dimethylethyloxycarbonyloxy, 2,2dimethylpropyloxycarbonyloxy, pyridin-2-ylcarbonyloxy, pyridin-3 -ylcarbonyloxy, pyridin-4-ylcarbonyloxy, 4-trifluoromethylpyridin-3-ylcarbonyloxy, allylcarbonyloxy, 5 methylsulfonyloxy, ethylsulfonyloxy, n-propylsulfonyloxy, 1 -methylethylsulfonyloxy, cyclopropylsulfonyloxy,
    R6 represents hydrogen,
    W represents oxygen and
    Q represents one of the moieties Q-l. 1 to Q-29.5 specifically mentioned in the table below:
    _N. tr -N. 5-Γ .N. /—s -N. Q-l.l Q-1.2 Q-l.3 Q-l.4 Q-l.5
    -N. y—s χΝ. F F Q-l.6 Q-l.7 Q-l.8 Q-l.9 Q-l.10
    -N. ,N. yr —s Q-l.11 Q-l.12 Q-l.13 Q-l.14 Q-l.15 /—s O—-/ / χΝ. χΝ. yr <Fci χΝ. N^r /~s Q-l.16 Q-l.17 Q-l.18 Q-l.19 Q-l.20
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    X *=N S F X s X F X s A Q-2.1 Q-2.2 Q-2.3 Q-2.4 Q-2.5
    X s ^=N X F X — s y/ X — s y^ </r· X syd Q-2.6 Q-2.7 Q-2.8 Q-2.9 Q-2.10
    X «yd~ X d X S d S y- X syd Q-2.11 Q-2.12 Q-2.13 Q-2.14 Q-2.15
    d Vs X S\Y^ 2=N —s X ~ d X f X \dr d Cl Q-2.16 Q-2.17 Q-2.18 Q-2.19 Q-2.20
    X X ~ X ~ yr X rd X F^ Q-3.1 Q-3.2 Q-3.3 Q-3.4 Q-3.5
    X sz X ¥ X ~ dr X ~ F X F Q-3.6 Q-3.7 Q-3.8 Q-3.9 Q-3.10
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    -N ~ z -N χΝ. s' Q-3.11 Q-3.12 Q-3.13 Q-3.14 Q-3.15
    -N ~ s' o ,N. —s .N. — s' *XJ Cl χΝ. o cr Q-3.16 Q-3.17 Q-3.18 Q-3.19 Q-3.20
    V V Q-4.1 Q-4.2 Q-4.3 Q-4.4 Q-4.5
    χδ__, z z z z LL Q-4.6 Q-4.7 Q-4.8 Q-4.9 Q-4.10
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    Z z z z $7 Q-4.11 Q-4.12 Q-4.13 Q-4.14 Q-4.15
    <z 7T Q-4.16 Q-4.17 Q-4.18 Q-4.19 Q-4.20
    .N .N. Zz .N. vr .N. Q-5.1 Q-5.2 Q-5.3 Q-5.4 Q-5.5
    Zr GV GV .N. Q-5.6 Q-5.7 Q-5.8 Q-5.9 Q-5.10
    Gy- FZZ Gy- V Q-5.11 Q-5.12 Q-5.13 Q-5.14 Q-5.15
    O-f^- F F °zz Q-5.16 Q-5.17 Q-5.18 Q-5.19 Q-5.20
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    .N. .N. >r .N. / 0 .N. .N. Q-6.1 Q-6.2 Q-6.3 Q-6.4 Q-6.5
    .N. / 0 .N. A -N ~ -N .N. — Rr Q-6.6 Q-6.7 Q-6.8 Q-6.9 Q-6.10
    .N. jr .N. .N. ~ A .N. A .N. Q-6.11 Q-6.12 Q-6.13 Q-6.14 Q-6.15
    .N. 1Γ o—/ / .N. .N. ~ .N. ~ yr <^CI .N. A Q-6.16 Q-6.17 Q-6.18 Q-6.19 Q-6.20
    ir o .N. >r 0 Cl .N. V/ <r o '—N .N. vr 0-°' Q-6.21 Q-6.22 Q-6.23 Q-6.24 Q-6.25
    _N '=N .N ό A .N o' V-*' .N o V·^ A ZNV — o 0-- Q-7.1 Q-7.2 Q-7.3 Q-7.4 Q-7.5
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    o —/~~^=N -N _N. — O' _N. — <r ZNK tv t- Q-7.6 Q-7.7 Q-7.8 Q-7.9 Q-7.10
    AL tv d tv & 0 f XN. tv _N. tv d~ Q-7.11 Q-7.12 Q-7.13 Q-7.14 Q-7.15
    ZN. tv 4 ZNK o' /tr ZNV ~ o' A tv £ A tv Cl Q-7.16 Q-7.17 Q-7.18 Q-7.19 Q-7.20
    ZN. tv ZNV tv ZNK v Q-8.1 Q-8.2 Q-8.3 Q-8.4 Q-8.5
    Λ o A zN^ r zN^ <F ZNK Q-8.6 Q-8.7 Q-8.8 Q-8.9 Q-8.10
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    f -N — 0 *XJ Cl ZNK O cr Q-8.16 Q-8.17 Q-8.18 Q-8.19 Q-8.20
    XN. -N. ,r XN. -Γ NC \ —0 r° Q-8.36 Q-8.37 Q-8.38 Q-8.39 Q-8.40
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    ο ' O o \ χΝ. o y-* 'A—OH o' -N. ο nh2 o' XN. o' V-r f3c Q-8.46 Q-8.47 Q-8.48 Q-8.49 Q-8.50
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    .N. tr Zr .N. 7Z Q-9.1 Q-9.2 Q-9.3 Q-9.4 Q-9.5
    .N. Yr .N. Yr .A z Q-9.6 Q-9.7 Q-9.8 Q-9.9 Q-9.10
    XNK cv ____,A .,, xA CIZ xA Q-9.11 Q-9.12 Q-9.13 Q-9.14 Q-9.15
    Yr tr Yr xA — Yr Q-9.16 Q-9.17 Q-9.18 Q-9.19 Q-9.20
    xA vr xA xA £F xA ~ Y Q-10.1 Q-10.2 Q-10.3 Q-10.4 Q-10.5
    Y^ V-T xA Y Q-10.6 Q-10.7 Q-10.8 Q-10.9 Q-10.10
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    Vr 0 V 0 Q-10.11 Q-10.12 Q-10.13 Q-10.14 Q-10.15
    V y—o Q 0 V? 0 F Q-10.16 Q-10.17 Q-10.18 Q-10.19 Q-10.20
    <r Λν / N 0^ X Q-ll.l Q-11.2 Q-11.3 Q-11.4 Q-11.5
    0 0^ £ <V' Z Cr 0-^ 0 Q-11.6 Q-11.7 Q-11.8 Q-11.9 Q-11.10
    0^ 0 'A: LL 0^ /“N 0—f / ;V' 0 Cl Q-ll.ll Q-11.12 Q-11.13 Q-11.14 Q-11.15
    0 Q-12.1 Q-12.2 Q-12.3 Q-12.4 Q-12.5
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    z Z z z z Q-12.6 Q-12.7 Q-12.8 Q-12.9 Q-12.10
    z LL z z z z Q-12.11 Q-12.12 Q-12.13 Q-12.14 Q-12.15
    ~7\ Cl ir ~A Br ~\~\ Q-12.16 Q-12.17 Q-12.18 Q-12.19 Q-12.20
    z jZ F F Q-12.26 Q-12.27 Q-12.28 Q-12.29 Q-12.30
    _ X -. _ X jZ _ X _ X _ X x 'y-·' Q-13.1 Q-13.2 Q-13.3 Q-13.4 Q-13.5
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    A A; _ XN. A' A F Q-13.6 Q-13.7 Q-13.8 Q-13.9 Q-13.10
    _ XNK ~ 00 \ XNV /Tn ’y-* Q-13.11 Q-13.12 Q-13.13 Q-13.14 Q-13.15
    kp- Ar/y^ Q-13.16 Q-13.17 Q-13.18 Q-13.19 Q-13.20
    -N. hnx y-* _N. HN _ xk ^-N ·γ-* ,N. hnz F Π A A / Q-13.21 Q-13.22 Q-13.23 Q-13.24 Q-13.25
    -N — _ x&k ^n -y-*’ a—-/ ,N HN _ /k '-ν' y--' -N HN 'V''^ Q-13.36 Q-13.37 Q-13.38 Q-13.39 Q-13.40
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    xNv '-N y-* Q-13.36 Q-13.37 Q-13.38 Q-13.39 Q-13.40
    .N. HNZ Vr -N. HN y-* χΝ. HN X χΝ. HN 'V-*' X -N. HN y-* F Q-13.41 Q-13.42 Q-13.43 Q-13.44 Q-13.45
    _N. HN Ύ* X —s' _ XN-v ^-n y-* F _ χΝ. N\ Ff\ .N. HN\ Ff\ Q-13.46 Q-13.47 Q-13.48 Q-13.49 Q-13.50
    χΝκ ^-n y- nc~a _ x*k ^-n y-*’ A XNK - _ xNv y-* Q-13.51 Q-13.52 Q-13.53 Q-13.54 Q-13.55
    X*k f-^z-n XNK F X LL Q-13.56 Q-13.57 Q-13.58 Q-13.59 Q-13.60
    _ XNV ^n y-*’ F F qir .N. -ςτ XN. -, _N. — X Q-13.61 Q-13.62 Q-13.63 Q-13.64 Q-13.65
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    _ Av ^-n y-*' J>° Ο'Υγ'·' —o CXzy* HO fl. Q-13.66 Q-13.67 Q-13.68 Q-13.69 Q-13.70
    _ Av — ^-n y-*’ o \ A nA A Cl Q-13.76 Q-13.77 Q-13.78 Q-13.79 Q-13.80
    Av tr \ Av tr Av cr r ir A tr a Q-14.1 Q-14.2 Q-14.3 Q-14.4 Q-14.5
    Av ~ A zr \ Av ir «—N \ «—N \ Q-14.6 Q-14.7 Q-14.8 Q-14.9 Q-14.10
    Av ~ GT Νχ__ Av N \ Av ~ j-r Q-14.11 Q-14.12 Q-14.13 Q-14.14 Q-14.15
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    tr H z H .N. tr Λ H H Q-14.16 Q-14.17 Q-14.18 Q-14.19 Q-14.20
    .N. <jr H Zr H N—J H N—J H H Q-15.1 Q-15.2 Q-15.3 Q-15.4 Q-15.5
    _N. ΌΤ / Ύτ / N—J / Hr / / Q-15.6 Q-15.7 Q-15.8 Q-15.9 Q-15.10
    -N JT .N. K -N. Λ A. Q-15.11 Q-15.12 Q-15.13 Q-15.14 Q-15.15
    _N. - Or V / Ύζ Λ Ύζ Cr 0 Q-15.16 Q-15.17 Q-15.18 Q-15.19 Q-15.20
    Hr N—J / yr Oyr N—J / _N. co- .N. <f.r Q-15.21 Q-15.22 Q-15.23 Q-15.24 Q-15.25
    _N. ' N XZ .N. 0 Cl c,0 /’
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    Q-15.26 Q-15.27 Q-15.28 Q-15.29 Q-15.30
    tr <r cr cr N Cr Q-16.1 Q-16.2 Q-16.3 Q-16.4 Q-16.5
    if T o / fTf Q-16.11 Q-16.12 Q-16.13 Q-16.14 Q-16.15
    eXr Cl -ΐ Q-16.21 Q-16.22 Q-16.23 Q-16.24 Q-16.25
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    X LL ? ό-Α '—o \ Q-16.41 Q-16.42 Q-16.43 Q-l 6.44 Q-16.45
    .AC aXr Π a^r Cl F Cl Q-16.46 Q-16.47 Q-16.48 Q-16.49 Q-16.50
    ν*νχ_-^ f n*NV* ci^O^ N. _ xr N XX N Cl .XT Q-16.51 Q-16.52 Q-16.53 Q-16.54 Q-16.55
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    - 7 s r LL Cy f F y— n Γ Q-16.56 Q-16.57 Q-16.58 Q-16.59 Q-16.60
    Cl N>Ny- Φ N>NXr-*’ y Cl N>NXr-*’ 7 Q-16.66 Q-16.67 Q-16.68 Q-16.69 Q-16.70
    ψΟτ Ύ N*Ny- Cl^^x^ n*nV- h F Ν*Νγ- N*Ny- Cl^5^ F rF Q-16.71 Q-16.72 Q-16.73 Q-16.74 Q-16.75
    bAI Cl aj Xr Q-16.76 Q-16.77 Q-16.78 Q-16.79 Q-16.80
    (r Ύ-Τ Hr N—J N—J Q-17.1 Q-17.2 Q-17.3 Q-17.4 Q-17.5
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    N—J A N—J Ayy- N—J Q-17.6 Q-17.7 Q-17.8 Q-17.9 Q-17.10
    Zr N—J N—J Q-18.1 Q-18.2 Q-18.3 Q-18.4 Q-18.5
    N—J A N—J N—J Q-18.6 Q-18.7 Q-18.8 Q-18.9 Q-18.10
    Cx N—N H ΧΎ' N—N \ w N—N ) w N—N )- ΧΎ' N—N )v Q-19.1 Q-19.2 Q-19.3 Q-19.4 Q-19.5
    Aw N-N \ Axv- N-N H Ay N—N \ N—N \ -hr r N—N \ Q-19.6 Q-19.7 Q-19.8 Q-19.9 Q-19.10
    Aw N—N b \ N-N \ Ά-w N—N \ A~w N—N b Q-19.11 Q-19.12 Q-19.13 Q-19.14 Q-19.15
    -N o' K XN. o yn5 XN. .N. A .N. o' H Cl Q-20.1 Q-20.2 Q-20.3 Q-20.4 Q-20.5
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    Co O-N z O'N Z “-N z Λν Zn Q-21.1 Q-22.2 Q-23.1 Q-23.2 Q-23.3
    z 0 z ZN z Z z , Z Q-23.4 Q-23.5 Q-23.6 Q-23.7 Q-23.8
    z Z z Z z ZN F F Co z A Q-23.9 Q-23.10 Q-23.11 Q-23.12 Q-23.13
    z z-N —o z z-N —s z ZN Cl F z c z d~ Q-23.14 Q-23.15 Q-23.16 Q-23.17 Q-23.18
    x z \ Z“N o /-N zs X “· 1 Z o—. z z o—. Q-23.19 Q-23.20 Q-23.21 Q-23.22 Q-23.23
    z r z ZN z A z Q z ZN °A Q-23.24 Q-23.25 Q-23.26 Q-23.27 Q-23.28
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    z-N z-N z-N z-N Cr Z_N s s s \ s s \ d d < o— F F F F F F F F Q-23.29 Q-23.30 Q-23.31 Q-23.32 Q-23.33
    z~N o ? o— £ d F F dr' d Vs d Q-23.34 Q-23.35 Q-23.36 Q-23.37 Q-23.38
    -Or d -Or rd d d o \ c F F Q-23.39 Q-23.40 Q-23.41 Q-23.42 Q-23.43
    -Or d d Cl O \/N O d o— Q-23.44 Q-23.45 Q-23.46 Q-23.47 Q-23.48
    <d 7 d oF o / Q-23.49 Q-23.50 Q-23.51 Q-23.52 Q-23.53
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    NH / °<N NH NH <i °<N NH ( o Q-23.54 Q-23.55 Q-23.56 Q-23.57 Q-23.58
    _n. _ fr N—N H _N. <'Y^ N—N / -N <'Y^ _ ^N—N N—N / _N. N—N Λ Q-25.1 Q-25.2 Q-25.3 Q-25.4 Q-25.5
    N—N / Zr N—N / N—N / -N. N—N /--y .N. /Γ N—N X Q-25.6 Q-25.7 Q-25.8 Q-25.9 Q-25.10
    _N. <'Y^ N—N o—/ / .N. -N. N—N —o .N. fr χ^-Ν .N. f y^ N—N <f Q-25.11 Q-25.12 Q-25.13 Q-25.14 Q-25.15
    Z'V /N—N Zr N—N / ^N—N N—N Λ N—N 7( Q-25.16 Q-25.17 Q-25.18 Q-25.19 Q-25.20
    _N. — fr N—N _N. — f y~ N—N 0 f3c _N. N—N 0 Cl _n. — N—N 0 cf3 X N—N 0 Cl Q-25.21 Q-25.22 Q-25.23 Q-25.24 Q-25.25
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    N—N 0 N—N 0 f3c N—N 0 Cl XT N—N 0 cf3 XT N—N 0 Cl Q-25.26 Q-25.27 Q-25.28 Q-25.29 Q-25.30
    F3c'^>Ny--* N—N 0 F-CW N—N 0 FsC F3C^.Ny^ N—N 0 Cl N—N 0 cf3 F-CW N—N 0 Cl Q-25.31 Q-25.32 Q-25.33 Q-25.34 Q-25.35
    N—N 0 Xr N—N 0 f3c Xr N—N 0 Cl Xr N—N 0 cf3 Xr* N-N 0 Cl Q-25.36 Q-25.37 Q-25.38 Q-25.39 Q-25.40
    Xr N—N 0· Xr N—N 0 N Xr N—N 01 Xr N-N 0 N N—N o Q-25.41 Q-25.42 Q-25.43 Q-25.44 Q-25.45
    N—N \ N—N N—N N—N \ N—N \ Q-26.1 Q-26.2 Q-26.3 Q-26.4 Q-26.5
    N—N \ -N. N—N r -N. i'T' N—N V Sy N—N \ N—N \ Q-26.6 Q-26.7 Q-26.8 Q-26.9 Q-26.10
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    N—N H -N. <Y^ N—N b <Y^ N—N b N—N \ N-N \ Q-26.11 Q-26.12 Q-26.13 Q-26.14 Q-26.15
    .N. er N—N \ .N. er N—N ) .N. N—N 0 .N. N—N .N. — ίΥ^ N—N Q-27.1 Q-27.2 Q-27.3 Q-27.4 Q-27.5
    N\ n N—N / N\ it I it N—N I it x. N—N λ /vN\ IT N—N ) Q-28.1 Q-28.2 Q-28.3 Q-28.4 Q-28.5
    N\ J N—J / N\ J ^N—7 Nt J N—J Nt J \ N— λ /A Q-29.1 Q-29.2 Q-29.3 Q-29.4 Q-29.5
  6. 6. The compound of the general formula (I) as claimed in claim 1 and/or the salt thereof, characterized in that
    X and Y independently of one another represent C-H or the moiety C-R1, where
    X represents C-H if Y represents the moiety C-R1 and
    10 X represents the moiety C-R1 if Y represents C-H,
    R1 represents methyl, ethyl, n-propyl, 1 -methylethyl, n-butyl, 1 -methylpropyl, 2methylpropyl, 1,1-dimethylethyl, n-pentyl, 1-methylbutyl, 2-methylbutyl, 3methylbutyl, 1,1 -dimethylpropyl, 1,2-dimethylpropyl, 2,2-dimethylpropyl, 1 15 ethylpropyl, n-hexyl, 1-methylpentyl, 2-methylpentyl, 3-methylpentyl, 4-methylpentyl,
    1,1-dimethylbutyl, 1,2-dimethylbutyl, 1,3-dimethylbutyl, 2,2-dimethylbutyl, 2,3dimethylbutyl, 3,3-dimethylbutyl, 1-ethylbutyl, 2-ethylbutyl, 1,1,2-trimethylpropyl, 1,2,2-trimethylpropyl, 1 -ethyl-1 -methylpropyl, 1 -ethyl-2-methylpropyl, cyclopropyl,
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    254 cyclobutyl, cyclopentyl, cyclohexyl, adamantan-l-yl, adamantan-2-yl, 1methylcyclopropyl, 2-methylcyclopropyl, 2,2-dimethylcyclopropyl, 2,3dimethylcyclopropyl, 1,1 ’-bi(cyclopropyl)-1 -yl, 1,1 '-bi(cyclopropyl)-2-yl, 2'-methyll,l'-bi(cyclopropyl)-2-yl, 1-cyanocyclopropyl, 2-cyanocyclopropyl, 1-methylcyclobutyl, 2-methylcyclobutyl, 3-methylcyclobutyl, 3,3-dimethylcyclobut-l-yl, 3,3difluorocyclobut-1 -yl, 3-fluorocyclobut-l-yl, 2,2-difluorocycloprop-l-yl, 1fluorocycloprop-1 -yl, 2-fluorocycloprop-l-yl, 1-ethylcyclopropyl, 1-methylcyclohexyl,
    2- methylcyclohexyl, 3-methylcyclohexyl, 1-methoxycyclohexyl, 2-methoxycyclohexyl,
    3- methoxycyclohexyl, trifluoromethyl, pentafluoroethyl, 1,1,2,2-tetrafluoroethyl, heptafluoropropyl, nonafluorobutyl, chlorodifluoromethyl, difluoromethyl, 2,2difluoroethyl, 2,2,2-trifluoroethyl, difluoro-tert-butyl, methoxy, ethoxy, n-propyloxy, isopropyloxy, n-butyloxy, tert-butyloxy, methoxymethyl, ethoxymethyl, methoxyethyl, ethoxyethyl, trifluoromethoxy, difluoromethoxy, 2,2,2-trifluoroethoxy, 2,2difluoroethoxy, methylthio, ethylthio, trifluoromethylthio, pentafluoroethylthio, phenyl, phenyloxy, p-Clphenyloxy, thiophen-2-yl, thiophen-3-yl, pyridin-2-yl, pyridin-3-yl, pyridin-4-yl, furan-2-yl, furan-3-yl, cyclopropylmethyl, cyclobutylmethyl, cyclopentylmethyl, cyclohexylmethyl, ethenyl, 1-propenyl, 2-propenyl, 1methylethenyl, l-butenyl, 2-butenyl, 3-butenyl, 1-methyl-1-propenyl, 2-methyl-lpropenyl, 1-methyl-2-propenyl, 2-methyl-2-propenyl, 1-pentenyl, 2-pentenyl, 3pentenyl, 4-pentenyl, prop-2-en-l-yloxy, but-3-en-l-yloxy, pent-4-en-l-yloxy, ethynyl,
    1- propynyl, 2-propynyl, l-butynyl, 1-pentynyl, 1-hexynyl, 2-(trimethylsilyl)ethyn-l-yl,
    2- (triethylsilyl)ethyn-1 -yl, 2-(triisopropylsilyl)ethyn-1 -yl,
    R3 represents hydroxy, methoxy, ethoxy, n-propyloxy, 1 -methylethoxy, n-butyloxy, 1 methylpropyloxy, 2-methylpropyloxy, 1,1-dimethylethoxy, n-pentyloxy, cyclopropylmethoxy, cyclobutylmethoxy, cyclopentylmethoxy, cyclohexylmethoxy, benzyloxy, p-chlorophenylmethoxy, m-chlorophenylmethoxy, o-chlorophenylmethoxy, p-methoxyphenylmethoxy, methoxymethoxy, methoxyethoxy, methoxy-n-propyloxy, ethoxymethoxy, ethoxyethoxy, methylcarbonyloxy, ethylcarbonyloxy, npropylcarbonyloxy, 1-methylethylcarbonyloxy, n-butylcarbonyloxy, 1methylpropylcarbonyloxy, 2-methylpropylcarbonyloxy, 1,1 -dimethylethylcarbonyloxy, n-pentylcarbonyloxy, phenylcarbonyloxy, p-chlorophenylcarbonyloxy, mchlorophenylcarbonyloxy, o-chlorophenylcarbonyloxy, p-fluorophenylcarbonyloxy, mfluorophenylcarbonyloxy, o-fluorophenylcarbonyloxy, cyclopropylcarbonyloxy, cyclobutylcarbonyloxy, cyclopentylcarbonyloxy, cyclohexylcarbonyloxy, trifluoromethylcarbonyloxy, difluoromethylcarbonyloxy, methoxycarbonyloxy, ethoxycarbonyloxy, n-propyloxycarbonyloxy, isopropyloxycarbonyloxy, n
    WO 2018/114596
    PCT/EP2017/082832
    255 butyloxycarbonyloxy, 1,1-dimethylethyloxycarbonyloxy, 2,2dimethylpropyloxycarbonyloxy, pyridin-2-ylcarbonyloxy, pyridin-3-ylcarbonyloxy, pyridin-4-ylcarbonyloxy, 4-trifluoromethylpyridin-3-ylcarbonyloxy, allylcarbonyloxy, methylsulfonyloxy, ethylsulfonyloxy, n-propylsulfonyloxy, 1 -methylethylsulfonyloxy, cyclopropylsulfonyloxy,
    R6 represents hydrogen,
    W represents oxygen and
    Q represents one of the moieties Q-1.1 to Q-29.5 specifically mentioned, as claimed in claim 5.
  7. 7. The use of one or more compounds of the general formula (I) and/or salts thereof, as defined in any of claims 1 to 6, as herbicide and/or plant growth regulator.
  8. 8. A herbicidal and/or plant growth-regulating composition, characterized in that the composition comprises one or more compounds of the formula (I) and/or salts thereof as defined in any of claims 1 to 6, and one or more further substances selected from groups (i) and/or (ii), with (i) one or more further agrochemically active substances, selected from the group consisting of insecticides, acaricides, nematicides, further herbicides, fungicides, safeners, fertilizers and/or further growth regulators, (ii) one or more formulation auxiliaries customary in crop protection.
  9. 9. A method for controlling harmful plants or for regulating the growth of plants, characterized in that an effective amount
    - of one or more compounds of the formula (I) and/or salts thereof, as defined in any of claims 1 to 6, or
    - of a composition as claimed in claim 8, is applied to the plants, seeds of plants, the soil in which or on which the plants grow or the area under cultivation.
AU2017379281A 2016-12-22 2017-12-14 Substituted heteroaryl pyrrolones and salts thereof and use thereof as herbicidal active substances Abandoned AU2017379281A1 (en)

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